3,065 results match your criteria Beilstein Journal Of Organic Chemistry[Journal]


Disposable cartridge concept for the on-demand synthesis of turbo Grignards, Knochel-Hauser amides, and magnesium alkoxides.

Beilstein J Org Chem 2020 19;16:1343-1356. Epub 2020 Jun 19.

Department of Chemical and Life Sciences Engineering, Virginia Commonwealth University, Biotech Eight, 737 N. 5th St., Box 980100, Richmond, VA 23219, USA.

Magnesium organometallic reagents occupy a central position in organic synthesis. The freshness of these compounds is the key for achieving a high conversion and reproducible results. Common methods for the synthesis of Grignard reagents from metallic magnesium present safety issues and exhibit a batch-to-batch variability. Read More

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http://dx.doi.org/10.3762/bjoc.16.115DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC7308606PMC

Distinctive reactivity of -benzylidene-[1,1'-biphenyl]-2-amines under photoredox conditions.

Beilstein J Org Chem 2020 18;16:1335-1342. Epub 2020 Jun 18.

Department of Chemistry, Chung-Ang University, 84 Heukseok-ro, Dongjak-gu, Seoul 06974, Republic of Korea.

A simple photocatalytic method was developed for the synthesis of unsymmetrical 1,2-diamines by the unprecedented reductive coupling of -benzylidene-[1,1'-biphenyl]-2-amines with an aliphatic amine. The presence of a phenyl substituent in the aniline moiety of the substrate was critical for the reactivity. The reaction proceeded via radical-radical cross-coupling of α-amino radicals generated by proton-coupled single-electron transfer in the presence of an Ir photocatalyst. Read More

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http://dx.doi.org/10.3762/bjoc.16.114DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC7308614PMC

Highly selective Diels-Alder and Heck arylation reactions in a divergent synthesis of isoindolo- and pyrrolo-fused polycyclic indoles from 2-formylpyrrole.

Beilstein J Org Chem 2020 17;16:1320-1334. Epub 2020 Jun 17.

Departamento de Química Orgánica, Escuela Nacional de Ciencias Biológicas, Instituto Politécnico Nacional, Prolongación de Carpio y Plan de Ayala S/N, 11340 Mexico City, Mexico.

A highly regio-, chemo- and stereoselective divergent synthesis of isoindolo- and pyrrolo-fused polycyclic indoles is herein described, starting from 2-formylpyrrole and employing Diels-Alder and Heck arylation reactions. 3-(Benzyl-2-pyrrolyl)acrylates and 4-(pyrrol-2-yl)butenones underwent a highly Diels-Alder cycloaddition with maleimides to furnish octahydropyrrolo[3,4-]indoles, which served as precursors in the regioselective synthesis of aza-polycyclic skeletons via an intramolecular Heck arylation reaction. Through the latter reaction, the 3-(benzyl-2-pyrrolyl)acrylates give rise to 3-(pyrrolo[2,1-]isoindol-3-yl)acrylates. Read More

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http://dx.doi.org/10.3762/bjoc.16.113DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC7308616PMC

Synthesis of 3-substituted isoxazolidin-4-ols using hydroboration-oxidation reactions of 4,5-unsubstituted 2,3-dihydroisoxazoles.

Beilstein J Org Chem 2020 16;16:1313-1319. Epub 2020 Jun 16.

Institute of Organic Chemistry, Catalysis and Petrochemistry, Slovak University of Technology in Bratislava, Radlinského 9, 81237 Bratislava, Slovak Republic.

Isoxazolidines represent a very important class of N/O-containing heterocycles used as the key intermediates in the synthesis of more complex cyclic and acyclic compounds, including various biologically active molecules. Here, we present a fast and highly stereoselective approach towards both C-3/4- and C-3/4- isomers of 3-substituted isoxazolidin-4-ols. The strategy relies on a highly regio- and -stereoselective hydroboration-oxidation reaction of the 4,5-unsubstituted 2,3-dihydroisoxazoles with basic hydrogen peroxide. Read More

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http://dx.doi.org/10.3762/bjoc.16.112DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC7308612PMC

Photocatalytic trifluoromethoxylation of arenes and heteroarenes in continuous-flow.

Beilstein J Org Chem 2020 15;16:1305-1312. Epub 2020 Jun 15.

Micro Flow Chemistry and Synthetic Methodology, Department of Chemical Engineering and Chemistry, Eindhoven University of Technology, Het Kranenveld, Bldg 14 - Helix, 5600 MB Eindhoven, The Netherlands.

The first example of photocatalytic trifluoromethoxylation of arenes and heteroarenes under continuous-flow conditions is described. Application of continuous-flow microreactor technology allowed to reduce the residence time up to 16 times in comparison to the batch procedure, while achieving similar or higher yields. In addition, the use of inorganic bases was demonstrated to increase the reaction yield under batch conditions. Read More

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http://dx.doi.org/10.3762/bjoc.16.111DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC7308607PMC

[3 + 2] Cycloaddition with photogenerated azomethine ylides in β-cyclodextrin.

Beilstein J Org Chem 2020 12;16:1296-1304. Epub 2020 Jun 12.

Department of Organic Chemistry and Biochemistry, Ruđer Bošković Institute, Bijenička cesta 54, 10 000 Zagreb, Croatia. ; Tel: +385 12 4561 141.

Stability constants for the inclusion complexes of cyclohexylphthalimide and adamantylphthalimide with β-cyclodextrin (β-CD) were determined by H NMR titration, = 190 ± 50 M, and = 2600 ± 600 M, respectively. Photochemical reactivity of the inclusion complexes and was investigated, and we found out that β-CD does not affect the decarboxylation efficiency, while it affects the subsequent photochemical H-abstraction, resulting in different product distribution upon irradiation in the presence of β-CD. The formation of ternary complexes with acrylonitrile (AN) and or was also essayed by H NMR. Read More

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http://dx.doi.org/10.3762/bjoc.16.110DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC7296198PMC

Ferrocenyl-substituted tetrahydrothiophenes via formal [3 + 2]-cycloaddition reactions of ferrocenyl thioketones with donor-acceptor cyclopropanes.

Beilstein J Org Chem 2020 10;16:1288-1295. Epub 2020 Jun 10.

Technische Universität Braunschweig, Institute of Organic Chemistry, Hagenring 30, 38106 Braunschweig, Germany.

Ferrocenyl thioketones reacted with donor-acceptor cyclopropanes in dichloromethane at room temperature in the presence of catalytic amounts of Sc(OTf) yielding tetrahydrothiophene derivatives, products of formal [3 + 2]-cycloaddition reactions, in moderate to high yields. In all studied cases, dimethyl 2-arylcyclopropane dicarboxylates reacted with the corresponding aryl ferrocenyl thioketones in a completely diastereoselective manner to form single products in which (C-2)-Ar and (C-5)-ferrocenyl groups were oriented in a -fashion. In contrast, the same cyclopropanes underwent reaction with alkyl ferrocenyl thioketones to form nearly equal amounts of both diastereoisomeric tetrahydrothiophenes. Read More

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http://dx.doi.org/10.3762/bjoc.16.109DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC7296194PMC

Synthesis, antiinflammatory activity, and molecular docking studies of bisphosphonic esters as potential MMP-8 and MMP-9 inhibitors.

Beilstein J Org Chem 2020 8;16:1277-1287. Epub 2020 Jun 8.

Instituto de Química Aplicada, Universidad del Papaloapan. Tuxtepec, 68301, Mexico.

Bisphosphonic acids (or bisphosphonates) have been successfully used in the clinic treatment of bone diseases for over decades. Additionally, the antiinflammatory activity of these compounds has been gaining attention. In our previous work, we synthesized and in vivo evaluated the bisphosphonic esters and , finding a moderate edema inhibition upon oral and topical administration on BALB/c mice. Read More

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http://dx.doi.org/10.3762/bjoc.16.108DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC7296197PMC

Oxime radicals: generation, properties and application in organic synthesis.

Beilstein J Org Chem 2020 5;16:1234-1276. Epub 2020 Jun 5.

N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky Prospect 47, Moscow, 119991, Russia.

-Oxyl radicals (compounds with an N-O fragment) represent one of the richest families of stable and persistent organic radicals with applications ranging from catalysis of selective oxidation processes and mechanistic studies to production of polymers, energy storage, magnetic materials design and spectroscopic studies of biological objects. Compared to other -oxyl radicals, oxime radicals (or iminoxyl radicals) have been underestimated for a long time as useful intermediates for organic synthesis, despite the fact that their precursors, oximes, are extremely widespread and easily available organic compounds. Furthermore, oxime radicals are structurally exceptional. Read More

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http://dx.doi.org/10.3762/bjoc.16.107DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC7277713PMC

Synthesis of pyrrolidinedione-fused hexahydropyrrolo[2,1-]isoquinolines via three-component [3 + 2] cycloaddition followed by one-pot -allylation and intramolecular Heck reactions.

Beilstein J Org Chem 2020 4;16:1225-1233. Epub 2020 Jun 4.

Center for Green Chemistry and Department of Chemistry, University of Massachusetts Boston, 100 Morrissey Boulevard, Boston, MA 02125, USA.

Two kinds of [3 + 2] cycloaddition intermediates generated from the three-component reactions of 2-bromobenzaldehydes and maleimides with amino esters or amino acids were used for a one-pot -allylation and intramolecular Heck reactions to form pyrrolidinedione-fused hexahydropyrrolo[2,1-]isoquinolines. The multicomponent reaction was combined with one-pot reactions to make a synthetic method with good pot, atom and step economy. MeCN was used as a preferable green solvent for the reactions. Read More

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http://dx.doi.org/10.3762/bjoc.16.106DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC7277624PMC

Anthelmintic drug discovery: target identification, screening methods and the role of open science.

Beilstein J Org Chem 2020 2;16:1203-1224. Epub 2020 Jun 2.

Centre for Respiratory Biology, UCL Respiratory, Division of Medicine, University College London, Gower Street, London, WC1E 6BT, United Kingdom.

Helminths, including cestodes, nematodes and trematodes, are a huge global health burden, infecting hundreds of millions of people. In many cases, existing drugs such as benzimidazoles, diethylcarbamazine, ivermectin and praziquantel are insufficiently efficacious, contraindicated in some populations, or at risk of the development of resistance, thereby impeding progress towards World Health Organization goals to control or eliminate these neglected tropical diseases. However, there has been limited recent progress in developing new drugs for these diseases due to lack of commercial attractiveness, leading to the introduction of novel, more efficient models for drug innovation that attempt to reduce the cost of research and development. Read More

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http://dx.doi.org/10.3762/bjoc.16.105DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC7277699PMC

Activated carbon as catalyst support: precursors, preparation, modification and characterization.

Beilstein J Org Chem 2020 2;16:1188-1202. Epub 2020 Jun 2.

Department of Chemistry and Pharmacy, University of Regensburg, Universitätsstraße 31, 93040 Regensburg, Germany.

The preparation of activated carbon materials is discussed along selected examples of precursor materials, of available production and modification methods and possible characterization techniques. We evaluate the preparation methods for activated carbon materials with respect to its use as catalyst support and identify important parameters for metal loading. The considered carbon sources include coal, wood, agricultural wastes or biomass as well as ionic liquids, deep eutectic solvents or precursor solutions. Read More

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http://dx.doi.org/10.3762/bjoc.16.104DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC7277711PMC

Photocatalysis with organic dyes: facile access to reactive intermediates for synthesis.

Beilstein J Org Chem 2020 29;16:1163-1187. Epub 2020 May 29.

Laboratory of Catalysis and Organic Synthesis, Ecole Polytechnique Fédérale de Lausanne, EPFL, SB ISIC LCSO, BCH 4306 1015 Lausanne, Switzerland.

Organic dyes have emerged as a reliable class of photoredox catalysts. Their great structural variety combined with the easy fine-tuning of their electronic properties has unlocked new possibilities for the generation of reactive intermediates. In this review, we provide an overview of the available approaches to access reactive intermediates that employ organophotocatalysis. Read More

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http://dx.doi.org/10.3762/bjoc.16.103DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC7277890PMC

Development of fluorinated benzils and bisbenzils as room-temperature phosphorescent molecules.

Beilstein J Org Chem 2020 29;16:1154-1162. Epub 2020 May 29.

Faculty of Molecular Chemistry and Engineering, Kyoto Institute of Technology, Matsugasaki, Sakyo-ku, Kyoto 606-8585, Japan.

Pure organic phosphorescent molecules are attractive alternatives to transition-metal-complex-based phosphores for biomedical and technological applications owing to their abundance and nontoxicity. This article discloses the design, synthesis, and photophysical properties of fluorinated benzil and bisbenzil derivatives as potential pure organic room-temperature phosphorescent molecules. These compounds were separately converted from the corresponding fluorinated bistolanes via PdCl-catalyzed oxidation by dimethyl sulfoxide, while nonfluorinated bistolane provided the corresponding bisbenzil derivatives exclusively in a similar manner. Read More

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http://dx.doi.org/10.3762/bjoc.16.102DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC7277987PMC

Synthesis and properties of quinazoline-based versatile exciplex-forming compounds.

Beilstein J Org Chem 2020 28;16:1142-1153. Epub 2020 May 28.

Department of Polymer Chemistry and Technology, Kaunas University of Technology, K. Baršausko g. 59, Kaunas 51423, Lithuania.

Three compounds, bearing a quinazoline unit as the acceptor core and carbazole, dimethyldihydroacridine, or phenothiazine donor moieties, were designed and synthesized in two steps including a facile copper-catalyzed cyclization and a nucleophilic aromatic substitution reaction. The photophysical properties of the compounds, based on theoretical calculations and experimental measurements, as well as the electrochemical and thermal properties, are discussed. The synthesized compounds form glasses with glass-transition temperatures ranging from 116 °C to 123 °C. Read More

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http://dx.doi.org/10.3762/bjoc.16.101DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC7277797PMC

A smart deoxyribozyme-based fluorescent sensor for in vitro detection of androgen receptor mRNA.

Beilstein J Org Chem 2020 27;16:1135-1141. Epub 2020 May 27.

Laboratory of Solution Chemistry of Advanced Materials and Technologies, ITMO University, Lomonosova 9, St. Petersburg, 197101, Russian Federation.

Nowadays a variety of biosensors are widely used in different fields, including biomedical diagnostics and self-testing. Nucleic acid-based biosensors are typically applied to detect another nucleic acid, proteins, ions, and several other types of compounds. It is most promising to develop simple and effective biosensors for the use in situations where traditional methods are not available due to their complexity and laboriousness. Read More

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http://dx.doi.org/10.3762/bjoc.16.100DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC7277777PMC

The charge-assisted hydrogen-bonded organic framework (CAHOF) self-assembled from the conjugated acid of tetrakis(4-aminophenyl)methane and 2,6-naphthalenedisulfonate as a new class of recyclable Brønsted acid catalysts.

Beilstein J Org Chem 2020 26;16:1124-1134. Epub 2020 May 26.

Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, Vavilov Street 28, 119991 Moscow, Russian Federation.

The acid-base neutralization reaction of commercially available disodium 2,6-naphthalenedisulfonate (NDS, 2 equivalents) and the tetrahydrochloride salt of tetrakis(4-aminophenyl)methane (TAPM, 1 equivalent) in water gave a novel three-dimensional charge-assisted hydrogen-bonded framework (CAHOF, ). The framework was characterized by X-ray diffraction, TGA, elemental analysis, and H NMR spectroscopy. The framework was supported by hydrogen bonds between the sulfonate anions and the ammonium cations of NDS and protonated TAPM moieties, respectively. Read More

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http://dx.doi.org/10.3762/bjoc.16.99DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC7277948PMC

Synthesis of esters of diaminotruxillic bis-amino acids by Pd-mediated photocycloaddition of analogs of the Kaede protein chromophore.

Beilstein J Org Chem 2020 25;16:1111-1123. Epub 2020 May 25.

Instituto de Síntesis Química y Catálisis Homogénea, ISQCH (CSIC - Universidad de Zaragoza), Pedro Cerbuna 12, E-50009 Zaragoza, Spain.

The stereoselective synthesis of truxillic bis-amino esters from polyfunctional oxazolones is reported. The reaction of 4-(()-arylidene)-2-()-styryl-5(4)-oxazolones with Pd(OAc) resulted in -palladation and the formation of a dinuclear open-book complexes with carboxylate bridges, where the Pd atom is C^N bonded to the oxazolone. In the two exocyclic C=C bonds of the oxazolone are in a face-to-face arrangement, which is optimal for their [2 + 2] photocycloaddition. Read More

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http://dx.doi.org/10.3762/bjoc.16.98DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC7277947PMC

A cyclopeptide and three oligomycin-class polyketides produced by an underexplored actinomycete of the genus .

Beilstein J Org Chem 2020 25;16:1100-1110. Epub 2020 May 25.

Biotechnology Research Center and Department of Biotechnology, Toyama Prefectural University, 5180 Kurokawa, Imizu, Toyama 939-0398, Japan.

Aside from the well-studied conventional actinomycetes such as , the less investigated genera of actinomycetes also represent a promising source of natural products. Genome mining indicated that members of the underexplored genus , from which no secondary metabolites have been reported to date, may harbor the biosynthetic machinery for the formation of novel natural products. The strain RD062863, that is available at a public culture collection, was obtained and subjected to metabolite analysis, which resulted in the discovery of a novel cyclopeptide, pseudosporamide (), along with three new oligomycin-class polyketides, pseudosporamicins A-C (-). Read More

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http://dx.doi.org/10.3762/bjoc.16.97DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC7277628PMC

A simple and easy to perform synthetic route to functionalized thienyl bicyclo[3.2.1]octadienes.

Beilstein J Org Chem 2020 22;16:1092-1099. Epub 2020 May 22.

NMR Centre, Ruđer Bošković Institute, Bijenička cesta 54, 10000 Zagreb, Croatia.

In order to prepare novel polycyclic derivatives of bicyclo[3.2.1]octadiene systems fused with a thiophene ring, photochemical cyclization and aldol condensation reactions were carried out. Read More

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http://dx.doi.org/10.3762/bjoc.16.96DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC7277534PMC

Palladium-catalyzed regio- and stereoselective synthesis of aryl and 3-indolyl-substituted 4-methylene-3,4-dihydroisoquinolin-1()-ones.

Beilstein J Org Chem 2020 20;16:1084-1091. Epub 2020 May 20.

Facoltà di Bioscienze e Tecnologie Agro-alimentari e Ambientali, Università di Teramo, Via Balzarini 1, 64100 Teramo (Te), Italy.

Cascade cyclocarbopalladation of the readily available aryl/alkyl-substituted propargylic amides containing an aryl iodide moiety, followed by Suzuki-Miyaura coupling with arylboronic acids, allowed an efficient regio- and stereoselective synthesis of tetrasubstituted 4-methylene-3,4-dihydroisoquinolin-1(2)-ones. Moreover, cascade cyclocarbopalladation, followed by the reaction with 2-alkynyltrifluoroacetanilides, accomplished a double cyclization to afford challenging 4-methylene-3,4-dihydroisoquinolin-1(2)-ones bearing a 3-indolyl substituent through aminopalladation/reductive elimination. Read More

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http://dx.doi.org/10.3762/bjoc.16.95DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC7277796PMC

Synthesis and anticancer activity of bis(2-arylimidazo[1,2-]pyridin-3-yl) selenides and diselenides: the copper-catalyzed tandem C-H selenation of 2-arylimidazo[1,2-]pyridine with selenium.

Beilstein J Org Chem 2020 20;16:1075-1083. Epub 2020 May 20.

School of Pharmaceutical Sciences, Aichi Gakuin University, 1-100 Kusumoto-cho, Chikusa-ku, Nagoya 464-8650, Japan.

Most heteroaryl selenides and diselenides are biologically active, with some reported to act as antioxidants and show activities that are medicinally relevant; hence, the development of efficient methods for their synthesis is an important objective. Herein, a simple method for the synthesis of selenides and diselenides bearing imidazo[1,2-]pyridine rings and their anticancer activity are described. The double C-H selenation of imidazo[1,2-]pyridine with Se powder was catalyzed by CuI (10 mol %) ligated with 1,10-phenanthroline (10 mol %) at 130 °C under aerobic conditions. Read More

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http://dx.doi.org/10.3762/bjoc.16.94DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC7277930PMC

Synthesis of novel multifunctional carbazole-based molecules and their thermal, electrochemical and optical properties.

Beilstein J Org Chem 2020 19;16:1066-1074. Epub 2020 May 19.

WestCHEM, School of Chemistry, University of Glasgow, Joseph Black Building, G128QQ Glasgow, UK.

Two novel carbazole-based compounds and were synthesised as potential candidates for application in organic electronics. The materials were fully characterised by NMR spectroscopy, mass spectrometry, FTIR, thermogravimetric analysis, differential scanning calorimetry, cyclic voltammetry, and absorption and emission spectroscopy. Compounds and , both of which were amorphous solids, were stable up to 291 °C and 307 °C, respectively. Read More

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http://dx.doi.org/10.3762/bjoc.16.93DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC7277623PMC

Copper-based fluorinated reagents for the synthesis of CFR-containing molecules (R ≠ F).

Beilstein J Org Chem 2020 18;16:1051-1065. Epub 2020 May 18.

Normandie Univ, INSA Rouen, UNIROUEN, CNRS, COBRA (UMR 6014), 76000 Rouen, France.

Over the years, the development of new methodologies for the introduction of various fluorinated motifs has gained a significant interest due to the importance of fluorine-containing molecules in the pharmaceutical and agrochemical industries. In a world eager to eco-friendlier tools, the need for innovative methods has been growing. To address these two challenges, copper-based reagents were developed to introduce CFH, CFR, CFCH, CFPO(OEt) and CFSOPh motifs on a broad range of substrates. Read More

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http://dx.doi.org/10.3762/bjoc.16.92DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC7277540PMC

Fluorinated phenylalanines: synthesis and pharmaceutical applications.

Beilstein J Org Chem 2020 15;16:1022-1050. Epub 2020 May 15.

Chemistry Department, Faculty of Science, Alexandria University, P.O. Box 426, Alexandria, 21321, Egypt.

Recent advances in the chemistry of peptides containing fluorinated phenylalanines (Phe) represents a hot topic in drug research over the last few decades. ᴅ- or ʟ-fluorinated phenylalanines have had considerable industrial and pharmaceutical applications and they have been expanded also to play an important role as potential enzyme inhibitors as well as therapeutic agents and topography imaging of tumor ecosystems using PET. Incorporation of fluorinated aromatic amino acids into proteins increases their catabolic stability especially in therapeutic proteins and peptide-based vaccines. Read More

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http://dx.doi.org/10.3762/bjoc.16.91DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC7237815PMC
May 2020
2.762 Impact Factor

Copper-catalysed alkylation of heterocyclic acceptors with organometallic reagents.

Beilstein J Org Chem 2020 14;16:1006-1021. Epub 2020 May 14.

Stratingh Institute for Chemistry, University of Groningen, Nijenborgh 4, 9747 AG, Groningen, The Netherlands.

Copper-catalysed asymmetric C-C bond-forming reactions using organometallic reagents have developed into a powerful tool for the synthesis of complex molecules with single or multiple stereogenic centres over the past decades. Among the various acceptors employed in such reactions, those with a heterocyclic core are of particular importance because of the frequent occurrence of heterocyclic scaffolds in the structures of chiral natural products and bioactive molecules. Hence, this review focuses on the progress made over the past 20 years for heterocyclic acceptors. Read More

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http://dx.doi.org/10.3762/bjoc.16.90DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC7237809PMC

Suzuki-Miyaura cross coupling is not an informative reaction to demonstrate the performance of new solvents.

Authors:
James Sherwood

Beilstein J Org Chem 2020 13;16:1001-1005. Epub 2020 May 13.

Green Chemistry Centre of Excellence, Department of Chemistry, University of York, Heslington, YO10 5DD, UK.

The development and study of new solvents has become important due to a proliferation of regulations preventing or limiting the use of many conventional solvents. In this work, the suitability of the Suzuki-Miyaura reaction to demonstrate the usefulness of new solvents was evaluated, including Cyrene™, dimethyl isosorbide, ethyl lactate, 2-methyltetrahydrofuran (2-MeTHF), propylene carbonate, and γ-valerolactone (GVL). It was found that the cross coupling is often unaffected by the choice of solvent, and therefore the Suzuki-Miyaura reaction provides limited information regarding the usefulness of any particular solvent for organic synthesis. Read More

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http://dx.doi.org/10.3762/bjoc.16.89DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC7237806PMC

Aryl-substituted acridanes as hosts for TADF-based OLEDs.

Beilstein J Org Chem 2020 13;16:989-1000. Epub 2020 May 13.

Department of Polymer Chemistry and Technology, Kaunas University of Technology, Radvilenu pl. 19, LT-50254, Kaunas, Lithuania.

Four aryl-substituted acridan derivatives were designed, synthesized and characterized as electroactive materials for organic light emitting diodes based on emitters exhibiting thermally activated delayed fluorescence. These compounds possessed relatively high thermal stability with glass-transition temperatures being in the range of 79-97 °C. The compounds showed oxidation bands arising from acridanyl groups in the range of 0. Read More

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http://dx.doi.org/10.3762/bjoc.16.88DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC7237810PMC

Accelerating fragment-based library generation by coupling high-performance photoreactors with benchtop analysis.

Beilstein J Org Chem 2020 12;16:982-988. Epub 2020 May 12.

SpiroChem AG, Rosental area, WRO-1047-3, Mattenstrasse 24, 4058 Basel, Switzerland.

Herein we report a workflow coupling photoredox-nickel dual-catalyzed -arylation reactions to benchtop analysis for the efficient generation of fragment-based libraries. Technological advances in photoreactor design facilitated reliable and reproducible experimentation. Knowledge on the reactivity under previously reported reaction conditions of spirocyclic and strained heterocyclic building blocks, viewed as chemistry informers, could thus be rapidly accessed, identifying privileged or challenging scaffolds and paving the way for further exploration. Read More

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http://dx.doi.org/10.3762/bjoc.16.87DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC7237803PMC

Synthesis and properties of tetrathiafulvalenes bearing 6-aryl-1,4-dithiafulvenes.

Beilstein J Org Chem 2020 12;16:974-981. Epub 2020 May 12.

Department of Materials Science and Biotechnology, Graduate School of Science and Engineering, Ehime University, 3 Bunkyo-cho, Matsuyama, Ehime 790-8577, Japan.

Novel multistage redox tetrathiafulvalenes (TTFs) bearing 6-aryl-1,4-dithiafulvene moieties were synthesized by palladium-catalyzed direct C-H arylation. In the presence of a catalytic amount of Pd(OAc), P(-Bu)·HBF, and an excess of CsCO, the C-H arylation of TTF with several aryl bromides bearing 1,3-dithiol-2-ylidenes took place efficiently to produce the corresponding π-conjugated molecules. We also succeeded in the estimation of the oxidation potentials and number of electrons involved in each oxidation step of the obtained compounds by digital simulations. Read More

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http://dx.doi.org/10.3762/bjoc.16.86DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC7237811PMC
May 2020
2.762 Impact Factor

Pd-catalyzed asymmetric Suzuki-Miyaura coupling reactions for the synthesis of chiral biaryl compounds with a large steric substituent at the 2-position.

Beilstein J Org Chem 2020 11;16:966-973. Epub 2020 May 11.

School of Chemistry, Guangdong Key Lab of Chiral Molecules and Drug Discovery, Sun Yat-sen University, No. 135 Xingangxi Road, Guangzhou 510275, People's Republic of China.

Pd-catalyzed asymmetric Suzuki-Miyaura couplings of 3-methyl-2-bromophenylamides, 3-methyl-2-bromo-1-nitrobenzene and 1-naphthaleneboronic acids have been successfully developed and the corresponding axially chiral biaryl compounds were obtained in very high yields (up to 99%) with good enantioselectivities (up to 88% ee) under mild conditions. The chiral-bridged biphenyl monophosphine ligands developed by our group exhibit significant superiority to the naphthyl counterpart MOP in both reactivity and enantioselectivity control. The large steric hindrance from π-conjugated -substituents of the bromobenzene substrates and the Pd···O interaction between carbonyl and palladium seem essential to achieve high enantioselectivity. Read More

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http://dx.doi.org/10.3762/bjoc.16.85DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC7237804PMC

Fabclavine diversity in bacteria.

Beilstein J Org Chem 2020 7;16:956-965. Epub 2020 May 7.

Molekulare Biotechnologie, Fachbereich Biowissenschaften, Goethe Universität Frankfurt, Max-von-Laue-Str. 9, 60438 Frankfurt, Germany.

The global threat of multiresistant pathogens has to be answered by the development of novel antibiotics. Established antibiotic applications are often based on so-called secondary or specialized metabolites (SMs), identified in large screening approaches. To continue this successful strategy, new sources for bioactive compounds are required, such as the bacterial genera or . Read More

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http://dx.doi.org/10.3762/bjoc.16.84DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC7214866PMC

Recent applications of porphyrins as photocatalysts in organic synthesis: batch and continuous flow approaches.

Beilstein J Org Chem 2020 6;16:917-955. Epub 2020 May 6.

Departamento de Química, Universidade Federal de São Carlos, São Carlos, SP, 13565-905, Brazil.

In this review we present relevant and recent applications of porphyrin derivatives as photocatalysts in organic synthesis, involving both single electron transfer (SET) and energy transfer (ET) mechanistic approaches. We demonstrate that these highly conjugated photosensitizers show increasing potential in photocatalysis since they combine both photo- and electrochemical properties which can substitute available metalloorganic photocatalysts. Batch and continuous-flow approaches are presented highlighting the relevance of enabling technologies for the renewal of porphyrin applications in photocatalysis. Read More

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http://dx.doi.org/10.3762/bjoc.16.83DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC7214915PMC

Cation-induced ring-opening and oxidation reaction of photoreluctant spirooxazine-quinolizinium conjugates.

Beilstein J Org Chem 2020 5;16:904-916. Epub 2020 May 5.

Department of Chemistry and Biology, University of Siegen and Center of Micro- and Nanochemistry and Engineering (Cμ), Adolf-Reichwein-Str. 2, 57068 Siegen, Germany.

Two new spiroindolinonaphthoxazine derivatives with an electron-accepting styrylquinolizinium or styrylcoralyne unit, respectively, were synthesized, and the influence of such an arylvinyl substituent on the chemical and photochemical properties of the compounds was investigated. Specifically, these spirooxazines turned out to be resistant towards the photoinduced merocyanine formation, and the irradiation with light mainly led to photodegradation of the substrates. However, it was shown by colorimetric and fluorimetric screening assays as well as by detailed NMR spectroscopic and mass spectrometric studies that the addition of particular metal ions (Cu, Fe, and to a certain extent Hg) initially induced a ring-opening reaction that was irreversibly followed by a fast ring closure-deprotonation-oxidation sequence to give styryl-substituted naphthoxazole derivatives as the products quantitatively. Read More

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http://dx.doi.org/10.3762/bjoc.16.82DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC7214873PMC

Bipyrrole boomerangs via Pd-mediated tandem cyclization-oxygenation. Controlling reaction selectivity and electronic properties.

Beilstein J Org Chem 2020 4;16:895-903. Epub 2020 May 4.

Wydział Chemii, Uniwersytet Wrocławski, ul. F. Joliot-Curie 14, 50-383 Wrocław, Poland.

Boomerang-shaped bipyrroles containing donor-acceptor units were obtained through a tandem palladium-mediated reaction consisting of a cyclization step, involving double C-H bond activation, and a double α-oxygenation. The latter reaction can be partly suppressed for the least reactive systems, providing access to α-unsubstituted boomerangs for the first time. These "α-free" systems are highly efficient fluorophores, with emission quantum yields exceeding 80% in toluene. Read More

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http://dx.doi.org/10.3762/bjoc.16.81DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC7214875PMC
May 2020
2.762 Impact Factor

Synthesis of new asparagine-based glycopeptides for future scanning tunneling microscopy investigations.

Beilstein J Org Chem 2020 30;16:888-894. Epub 2020 Apr 30.

Institute of Organic Chemistry, University of Tübingen, Auf der Morgenstelle 18, 72076 Tübingen, Germany.

For investigations on the biological functions of oligosaccharides and peptidomimetics, new asparagine-based mono- and disaccharides containing glycopeptides were prepared in solution. The applicability of two common peptide coupling reagents, using an orthogonal Fmoc/-Bu strategy along with acetyl protecting groups for the carbohydrate moiety, was studied. Thus, the prepared libraries of glycopeptides were designed as model systems of cell surfaces for future investigations by combined preparative mass spectroscopy and scanning tunneling microscopy (STM) using soft-landing electrospray beam deposition (ES-IBD), on metal surfaces. Read More

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http://dx.doi.org/10.3762/bjoc.16.80DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC7214877PMC

Diversity-oriented synthesis of 17-spirosteroids.

Beilstein J Org Chem 2020 28;16:880-887. Epub 2020 Apr 28.

Unité Molécules de Communication et Adaptations des Micro-organismes (MCAM), Muséum National d'Histoire Naturelle, CNRS, Paris, France.

A diversity-oriented synthesis (DOS) approach has been used to functionalize 17-ethynyl-17-hydroxysteroids through a one-pot procedure involving a ring-closing enyne metathesis (RCEYM) and a Diels-Alder reaction on the resulting diene, under microwave irradiations. Taking advantage of the propargyl alcohol moiety present on commercially available steroids, this classical strategy was applied to mestranol and lynestrenol, giving a collection of new complex 17-spirosteroids. Read More

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http://dx.doi.org/10.3762/bjoc.16.79DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC7214869PMC

A method to determine the correct photocatalyst concentration for photooxidation reactions conducted in continuous flow reactors.

Beilstein J Org Chem 2020 27;16:871-879. Epub 2020 Apr 27.

Corning European Technology Center, 7 Bis Avenue de Valvins, F-77215 Avon Cedex, France.

When conducting a photooxidation reaction, the key question is what is the best amount of photocatalyst to be used in the reaction? This work demonstrates a fast and simple method to calculate a reliable concentration of the photocatalyst that will ensure an efficient reaction. The determination is based on shifting the calculation away from the concentration of the compound to be oxidized to utilizing the limitations on the total light dose that can be delivered to the catalyst. These limitations are defined by the photoflow setup, specifically the channel height and the emission peak of the light source. Read More

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http://dx.doi.org/10.3762/bjoc.16.78DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC7214865PMC
April 2020
2.762 Impact Factor

Copper catalysis with redox-active ligands.

Beilstein J Org Chem 2020 24;16:858-870. Epub 2020 Apr 24.

Université de Strasbourg, Institut de Chimie, UMR CNRS 7177, 67000 Strasbourg, France.

Copper catalysis finds applications in various synthetic fields by utilizing the ability of copper to sustain mono- and bielectronic elementary steps. Further to the development of well-defined copper complexes with classical ligands such as phosphines and N-heterocyclic carbenes, a new and fast-expanding area of research is exploring the possibility of a complementing metal-centered reactivity with electronic participation by the coordination sphere. To achieve this electronic flexibility, redox-active ligands can be used to engage in a fruitful "electronic dialogue" with the metal center, and provide additional venues for electron transfer. Read More

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http://dx.doi.org/10.3762/bjoc.16.77DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC7214867PMC

Aldehydes as powerful initiators for photochemical transformations.

Beilstein J Org Chem 2020 23;16:833-857. Epub 2020 Apr 23.

Laboratory of Organic Chemistry, Department of Chemistry, National and Kapodistrian University of Athens, Athens 15784, Greece.

Photochemistry, the use of light to promote organic transformations, has been known for more than a century but only recently has revolutionized the way modern chemists are thinking. Except from transition metal-based complexes, small organic molecules have been introduced as catalysts or initiators. In this review, we summarize the potential that (aromatic or aliphatic) aldehydes have as photoinitiators. Read More

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http://dx.doi.org/10.3762/bjoc.16.76DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC7188926PMC

Preparation of 2-phospholene oxides by the isomerization of 3-phospholene oxides.

Beilstein J Org Chem 2020 22;16:818-832. Epub 2020 Apr 22.

Department of Organic Chemistry and Technology, Budapest University of Technology and Economics, Műegyetem rkp. 3., H-1111 Budapest, Hungary.

A series of 1-substituted-3-methyl-2-phospholene oxides was prepared from the corresponding 3-phospholene oxides by double bond rearrangement. The 2-phospholene oxides could be obtained by heating the 3-phospholene oxides in methanesulfonic acid, or via the formation of cyclic chlorophosphonium salts. Whereas mixtures of the 2- and 3-phospholene oxides formed, when the isomerization of 3-phospholene oxides was attempted under thermal conditions, or in the presence of a base. Read More

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http://dx.doi.org/10.3762/bjoc.16.75DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC7189000PMC

Photocatalytic deaminative benzylation and alkylation of tetrahydroisoquinolines with -alkylpyrydinium salts.

Beilstein J Org Chem 2020 21;16:809-817. Epub 2020 Apr 21.

Institute of Applied Synthetic Chemistry, TU Wien, Getreidemarkt 9/163, 1060 Vienna, Austria.

A ruthenium-catalyzed photoredox coupling of substituted -aryltetrahydroisoquinolines (THIQs) and different bench-stable pyridinium salts was successfully developed to give fast access to 1-benzyl-THIQs. Furthermore, secondary alkyl and allyl groups were also successfully introduced via the same method. Additionally, the typically applied -phenyl group in the THIQ substrate could be replaced by the cleavable -methoxyphenyl (PMP) group and successful N-deprotection was demonstrated. Read More

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http://dx.doi.org/10.3762/bjoc.16.74DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC7189001PMC
April 2020
2.762 Impact Factor

Efficient synthesis of piperazinyl amides of 18β-glycyrrhetinic acid.

Beilstein J Org Chem 2020 21;16:798-808. Epub 2020 Apr 21.

College of Public Basic Sciences, Jinzhou Medical University, Jinzhou, 121001, China.

In the present study, a practical method to prepare piperazinyl amides of 18β-glycyrrhetinic acid was developed. Two main procedures for the construction of important intermediate are discussed. One procedure involves the amidation of 1-Boc-piperazine with 3-acetyl-18β-glycyrrhetinic acid, prepared by the reaction of 18β-glycyrrhetinic acid with acetic anhydride without any solvent at 130 °C. Read More

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http://dx.doi.org/10.3762/bjoc.16.73DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC7188925PMC

One-pot synthesis of dicyclopenta-fused peropyrene via a fourfold alkyne annulation.

Beilstein J Org Chem 2020 20;16:791-797. Epub 2020 Apr 20.

Center for Advancing Electronics Dresden (cfaed) & Faculty of Chemistry and Food Chemistry, Technische Universität Dresden, 01062 Dresden, Germany.

A novel dicyclopenta-fused peropyrene derivative was synthesized via a palladium-catalyzed four-fold alkyne annulation of 1,3,6,8-tetrabromo-2,7-diphenylpyrene () with diphenylacetylene. The annulative π-extension reaction toward involved a twofold [3 + 2] cyclopentannulation and subsequent twofold [4 + 2] benzannulation. The structure of is unambiguously confirmed by X-ray crystallography; adopted a twisted geometry due to the steric hindrance of the phenyl rings and the hydrogen substituents at the bay regions. Read More

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http://dx.doi.org/10.3762/bjoc.16.72DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC7188986PMC

Reaction of indoles with aromatic fluoromethyl ketones: an efficient synthesis of trifluoromethyl(indolyl)phenylmethanols using KCO/BuPBr in water.

Beilstein J Org Chem 2020 20;16:778-790. Epub 2020 Apr 20.

Institute of Inorganic Chemistry, University of Bonn, Gerhard-Domagk-Str. 1, D-53121 Bonn, Germany.

A new, mild and efficient protocol for the synthesis of trifluoromethyl(indolyl)phenylmethanols by the reaction of indoles with a variety of aromatic fluoromethyl ketones in the presence of KCO (15 mol %) and BuPBr (15 mol %) in water. The desired products were obtained in good to excellent yields without requiring a column chromatographic purification. The reusability of the catalytic system and large-scale synthesis of indolyl(phenyl)methanols, which would further transform into biological active indole-derived compounds, are further advantages of this protocol. Read More

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http://dx.doi.org/10.3762/bjoc.16.71DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC7189012PMC

Towards triptycene functionalization and triptycene-linked porphyrin arrays.

Beilstein J Org Chem 2020 17;16:763-777. Epub 2020 Apr 17.

School of Chemistry, SFI Tetrapyrrole Laboratory, Trinity Biomedical Sciences Institute, 152-160 Pearse Street, Trinity College Dublin, The University of Dublin, Dublin 2, Ireland.

Herein, 9,10-diethynyltriptycene is investigated for its use as a rigid isolating unit in the synthesis of multichromophoric arrays. Sonogashira cross-coupling conditions are utilized to attach various porphyrins and boron dipyrromethenes (BODIPYs) to the triptycene scaffold. While there are previous examples of triptycene porphyrin complexes, this work reports the first example of a linearly connected porphyrin dimer, linked through the bridgehead carbons of triptycene. Read More

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http://dx.doi.org/10.3762/bjoc.16.70DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC7176921PMC

Efficient synthesis of dipeptide analogues of α-fluorinated β-aminophosphonates.

Beilstein J Org Chem 2020 16;16:756-762. Epub 2020 Apr 16.

Faculty of Chemistry, Adam Mickiewicz University in Poznań, Uniwersytetu Poznańskiego 8, 61-614 Poznań, Poland.

Herein, we present an efficient synthesis of dipeptide analogues of α-fluorinated β-aminophosphonates. Each step of the synthesis was optimized to provide excellent yields. Moreover, the absolute configuration of the obtained compounds was determined by X-ray analysis, which proved the stereochemistry that was proposed based on NMR studies. Read More

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http://dx.doi.org/10.3762/bjoc.16.69DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC7176923PMC

Combining enyne metathesis with long-established organic transformations: a powerful strategy for the sustainable synthesis of bioactive molecules.

Beilstein J Org Chem 2020 16;16:738-755. Epub 2020 Apr 16.

Laboratory of Catalysis, Institut de Chimie (B6a), Allée du six Août 13, Université de Liège, 4000 Liège, Belgium.

This account surveys the current progress on the application of intra- and intermolecular enyne metathesis as main key steps in the synthesis of challenging structural motifs and stereochemistries found in bioactive compounds. Special emphasis is placed on ruthenium catalysts as promoters of enyne metathesis to build the desired 1,3-dienic units. The advantageous association of this approach with name reactions like Grignard, Wittig, Diels-Alder, Suzuki-Miyaura, Heck cross-coupling, etc. Read More

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http://dx.doi.org/10.3762/bjoc.16.68DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC7176922PMC

Recent advances in Cu-catalyzed C(sp)-Si and C(sp)-B bond formation.

Beilstein J Org Chem 2020 15;16:691-737. Epub 2020 Apr 15.

Department of Chemistry & Biochemistry, University of California, Santa Barbara, California 93106, USA.

Numerous reactions generating C-Si and C-B bonds are in focus owing to the importance of incorporating silicon or boron into new or existing drugs, in addition to their use as building blocks in cross-coupling reactions en route to various targets of both natural and unnatural origins. In this review, recent protocols relying on copper-catalyzed sp carbon-silicon and carbon-boron bond-forming reactions are discussed. Read More

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http://dx.doi.org/10.3762/bjoc.16.67DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC7176932PMC
April 2020
2.762 Impact Factor

Synthesis of C-fragment buckybowls bearing alkoxy substituents.

Beilstein J Org Chem 2020 15;16:681-690. Epub 2020 Apr 15.

Division of Applied Chemistry, Graduate School of Engineering, Osaka University, 2-1 Yamadaoka, Suita, Osaka 565-0871, Japan.

Buckybowls bearing a C fragment having two alkoxy groups were synthesized and their structural and optical properties were investigated by single crystal X-ray analysis and UV-vis spectroscopy. In the synthesis of dioxole derivative , the regioisomer was also produced. The yield of was increased by increasing the reaction temperature, indicating that the rearrangement might involve the equilibrium between the Pd(IV) intermediates through C-H bond activation. Read More

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http://dx.doi.org/10.3762/bjoc.16.66DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC7176931PMC