349 results match your criteria alkynes homogeneous

Metal Nanoparticles Immobilized on Molecularly Modified Surfaces: Versatile Catalytic Systems for Controlled Hydrogenation and Hydrogenolysis.

Acc Chem Res 2021 May 6;54(9):2144-2157. Epub 2021 Apr 6.

Max Planck Institute for Chemical Energy Conversion, Stiftstraße 34-36, 45470 Mülheim an der Ruhr, Germany.

ConspectusThe synthesis and use of supported metal nanoparticle catalysts have a long-standing tradition in catalysis, typically associated with the field of heterogeneous catalysis. More recently, the development and understanding of catalytic systems composed of metal nanoparticles (NPs) that are synthesized from organometallic precursors on molecularly modified surfaces (MMSs) have opened a conceptually new approach to the design of multifunctional catalysts (NPs@MMS). These complex yet fascinating materials bridge molecular ("homogeneous") and material ("heterogeneous") approaches to catalysis and provide access to catalytic systems with tailor-made reactivity through judicious combinations of supports, molecular modifiers, and nanoparticle precursors. Read More

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Easy Access to Versatile Catalytic Systems for C-H Activation and Reductive Amination Based on Tetrahydrofluorenyl Rhodium(III) Complexes.

Chemistry 2021 Mar 29. Epub 2021 Mar 29.

A.N.Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Science, ul. Vavilova 28, 119991, Moscow, RUSSIAN FEDERATION.

On the basis of 1,2,3,4-tetrahydrofluorenyl ligand, a simple approach was developed to new effective rhodium catalysts for the construction of C-C and C-N bonds. The halide compounds [(η5-tetrahydrofluorenyl)RhX2]2 (2a: X = Br; 2b: X = I) were synthesized by treatment of the bis(ethylene) derivative (η5-tetrahydrofluorenyl)Rh(C2H4)2 (1a) with halogens. An analogous reaction of the cyclooctadiene complex (η5-tetrahydrofluorenyl)Rh(cod) (1b) with I2 is complicated by the side formation of [(cod)RhI]2. Read More

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Synthesis of Aminoallenes via Selenium-π-Acid-Catalyzed Cross-Coupling of -Fluorinated Sulfonimides with Simple Alkynes.

European J Org Chem 2021 Mar 8;2021(11):1720-1725. Epub 2021 Mar 8.

Faculty of Chemistry and Pharmacy University of Regensburg Universitätsstraße 31 93053 Regensburg Germany.

The facile synthesis of aminoallenes, accomplished by a selenium-π-acid-catalyzed cross-coupling of an -fluorinated sulfonimide with simple, non-activated alkynes, is reported. Until now, aminoallenes were difficult to be accessed by customary means, inasmuch as pre-activated and, in part, intricate starting materials were necessary for their synthesis. In sharp contrast, the current study shows that ordinary internal alkynes can serve as simple and readily available precursors for the construction of the aminoallene motif. Read More

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Robust Cobalt Catalyst for Nitrile/Alkyne [2+2+2] Cycloaddition: Synthesis of Polyarylpyridines and Their Mechanochemical Cyclodehydrogenation to Nitrogen-Containing Polyaromatics*.

Angew Chem Int Ed Engl 2021 Apr 12;60(17):9627-9634. Epub 2021 Mar 12.

Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore, 637371, Singapore.

The transition-metal-catalyzed [2+2+2] cycloaddition of nitriles and alkynes is an established synthetic approach to pyridines; however, these cycloadditions often rely on the use of tethered diynes or cyanoalkynes as one of the reactants. Thus, examples of efficient, fully intermolecular catalytic [2+2+2] pyridine synthesis, especially those employing unactivated nitriles and internal alkynes leading to pentasubstituted pyridines, remain scarce. Herein, we report on simple and inexpensive catalytic systems based on cobalt(II) iodide, 1,3-bis(diphenylphosphino)propane, and Zn that promote [2+2+2] cycloaddition of various nitriles and diarylacetylenes for the synthesis of a broad range of polyarylated pyridines. Read More

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Short-Chained Platinum Complex Catalyzed Hydrosilylation under Thermomorphic Conditions: Heterogeneous Phase Separation at Ice Temperature.

Molecules 2021 Jan 13;26(2). Epub 2021 Jan 13.

Institute of Organic and Polymeric Materials, National Taipei University of Technology, Taipei 106, Taiwan.

Homogeneous catalysts PtCl[5,5'-bis-(-ClCF(CF)CHOCH)-2,2'-bpy] () and PtCl[5,5'-bis-(-HCF(CF)CHOCH)-2,2'-bpy] (), which contained short fluorous chains, were synthesized and used in catalysis of hydrosilylation of alkynes. In these reactions the thermomorphic mode was effectively used to recover these catalysts from the reaction mixture up to eight cycles by taking advantage of heterogeneous phase separation at ice temperature. This kind of catalysis had previously been observed in fluorous catalysts of platinum containing about 50% F-content, but in this work the percentage of F-content is decreased to only about 30%, by which we termed them as "very light fluorous". Read More

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January 2021

Catalytic Enantioselective Aminopalladation-Heck Cascade.

Angew Chem Int Ed Engl 2021 03 17;60(13):7093-7097. Epub 2021 Feb 17.

Laboratory of Synthesis and Natural Products, Institute of Chemical Sciences and Engineering, Ecole Polytechnique Fédérale de Lausanne, EPFL-SB-ISIC-LSPN, BCH 5304, 1015, Lausanne, Switzerland.

Domino processes initiated by intramolecular nucleopalladation of alkynes have been developed into powerful synthetic tools for the synthesis of functionalized heterocycles. However, a catalytic enantioselective version of this class of reactions remains scarce. We report herein that reaction of 2-alkynylanilines with prochiral cyclopentenes in the presence of a catalytic amount of Pd(OAc) , a chiral bidentate pyrox ligand and O as terminal oxidant affords the structurally diverse indole-cyclopentene conjugates bearing two stereocenters in a highly diastereo- and enantio-selective manner. Read More

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Water-Soluble O-, S- and Se-Functionalized Cyclic Acetyl-triaza-phosphines. Synthesis, Characterization and Application in Catalytic Azide-alkyne Cycloaddition.

Molecules 2020 Nov 23;25(22). Epub 2020 Nov 23.

Centro de Química Estrutural, Instituto Superior Técnico, Universidade de Lisboa Av. Rovisco Pais, 1049-001 Lisboa, Portugal.

The 3,7-diacetyl-1,3,7-triaza-5-phosphabicyclo[3.3.1]nonane (DAPTA) derivatives, viz. Read More

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November 2020

Gold-Catalyzed Reactions of Specially Activated Alkynes, Allenes, and Alkenes.

Chem Rev 2020 Nov 23. Epub 2020 Nov 23.

Department of Chemistry and Biomolecular Sciences, University of Ottawa, K1N 6N5 Ottawa, Canada.

This review describes the gold-catalyzed reactions of specially activated alkynes, allenes, and alkenes. Such species are characterized by the presence of either electron-donating or electron-withdrawing groups as substituents of the carbon π-system. They are intrinsically polarized, and when compared to their nonspecially activated counterparts can therefore be involved in gold-catalyzed transformations featuring increased regio-, stereo-, and chemoselectivities. Read More

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November 2020

Organophosphorus and Iron Catalysis: Good Partners for Hydrometalation of Olefins and Alkynes.

J Org Chem 2020 Nov 10;85(22):14298-14306. Epub 2020 Nov 10.

Univ Rennes, CNRS, ISCR - UMR 6226, F-35000 Rennes, France.

The last decades have seen an impressive development of iron complexes involving organophosphorus ligands applied in homogeneous catalyzed hydrometalation of olefins and alkynes. Two main topics will be covered in this JOCSynopsis: (i) an overview of the achievements in the area of iron-catalyzed hydrophosphination and then (ii) hydrosilylation, hydroborylation, and hydromagnesiation reactions promoted by catalysts based on organophosphorus ligands and iron. Read More

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November 2020

(N),C,N-Coordinated Heavier Group 13-15 Compounds: Synthesis, Structure and Applications.

Chempluschem 2020 Oct;85(10):2320-2340

Department of General and Inorganic Chemistry, Faculty of Chemical Technology, University of Pardubice, Studentská 573, Pardubice 532 10, Czech Republic.

The aim of this review is to summarize recent achievements in the field of (N),C,N-coordinated group 13-15 compounds not only regarding their synthesis and structure, but mainly focusing on their potential applications. Relevant compounds contain various types of N-coordinating ligands built up on an ortho-(di)substituted phenyl platform. Thus, group 13 and 14 derivatives were used as single-source precursors for the deposition of semiconducting thin films, as building blocks for the preparation of high-molecular polymers with remarkable optical and chemical properties or as compounds with interesting reactivity in hydrometallation processes. Read More

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October 2020

Gold(I)-NHC-catalysed synthesis of benzofurans migratory cyclization of 2-alkynylaryl ethers.

Org Biomol Chem 2020 Oct;18(40):8186-8191

California State University Fresno, 2555 E San Ramon Ave M/S SB70, Fresno, CA 93740, USA.

Homogeneous cationic gold(i) catalysis emerged as a preferred avenue for the activation of alkenes and alkynes towards reactions with weak nucleophiles, especially in cyclization reactions. Here we report an intramolecular carboalkoxylation reaction of electron-rich benzyl ethers of 2-ethynylaryl phenols catalysed by a digold(i)-NHC complex. The reaction proceeds efficiently with low catalyst loading and the resulting 2,3-disubstituted benzofurans form in moderate to good yields. Read More

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October 2020

Gold-Catalyzed C-H Functionalization Polycondensation for the Synthesis of Aromatic Polymers.

Angew Chem Int Ed Engl 2020 Dec 3;59(49):21971-21975. Epub 2020 Nov 3.

School of Polymer Science and Engineering, The University of Southern Mississippi, 118 College Drive #5050, Hattiesburg, MS, 39406, USA.

Homogeneous gold (Au) complexes have demonstrated tremendous utility in modern organic chemistry; however, their application for the synthesis of polymers remains rare. Herein, we demonstrate the first catalytic application of Au complexes toward the polycondensation of alkyne-containing comonomers and heteroarene nucleophiles. Polymerization occurs through successive intermolecular hydroarylation reactions to produce high molecular weight aromatic copolymers with 1,1-disubstituted alkene backbone linkages. Read More

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December 2020

Efficient [(NHC)Au(NTf)]-catalyzed hydrohydrazidation of terminal and internal alkynes.

Beilstein J Org Chem 2020 26;16:2080-2086. Epub 2020 Aug 26.

Organometallic Chemistry, Technische Universität Darmstadt, Alarich-Weiss-Str. 12, 64287 Darmstadt, Germany.

The efficient hydrohydrazidation of terminal (-, 18 examples, 0.1-0.2 mol % [(NHC)Au(NTf)], = 60 °C) and internal alkynes (-, 10 examples, 0. Read More

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Simpler and Cleaner Synthesis of Variously Capped Cobalt Nanocrystals Applied in the Semihydrogenation of Alkynes.

Inorg Chem 2020 Oct 14;59(19):13972-13978. Epub 2020 Sep 14.

Sorbonne Université, CNRS, Institut Parisien de Chimie Moléculaire, UMR 8232, 4 place Jussieu, 75005 Paris, France.

Unlike the classical organometallic approach, we report here a synthetic pathway requiring no reducing sources or heating to produce homogeneous hexagonal-close-packed cobalt nanocrystals (Co NCs). Involving a disproportionation process, this simple and fast (6 min) synthesis is performed at room temperature in the presence of ecofriendly fatty alcohols to passivate Co NCs. Through a recycling step, the yield of Co NCs is improved and the waste generation is limited, making this synthetic route cleaner. Read More

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October 2020

Nitrene Transfer and Carbene Transfer in Gold Catalysis.

Chem Rev 2020 Aug 3. Epub 2020 Aug 3.

Department of Chemistry, National Tsing-Hua University, Hsinchu 30013, Taiwan, Republic of China.

Catalytic transformations involving metal carbenes are considered one of the most important aspects of homogeneous transition metal catalysis. Recently, gold-catalyzed generation of gold carbenes from readily available alkynes represents a significant advance in metal carbene chemistry. This Review summarizes the advances in the gold-catalyzed nitrene-transfer reactions of alkynes with nitrogen-transfer reagents, such as azides, nitrogen ylides, isoxazoles, and anthranils, and gold-catalyzed carbene-transfer reactions, involving oxygen atom-transfer reactions of alkynes with nitro compounds, nitrones, sulfoxides, and pyridine -oxides, through the presumable α-imino gold carbene and α-oxo gold carbene intermediates, respectively. Read More

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Recent Advances in Catalytic Hydrosilylations: Developments beyond Traditional Platinum Catalysts.

Angew Chem Int Ed Engl 2021 Jan 1;60(2):550-565. Epub 2020 Dec 1.

Leibniz-Institute for Catalysis, Albert-Einstein-Str. 29a, 18059, Rostock, Germany.

Hydrosilylation reactions, which allow the addition of Si-H to C=C/C≡C bonds, are typically catalyzed by homogeneous noble metal catalysts (Pt, Rh, Ir, and Ru). Although excellent activity and selectivity can be obtained, the price, purification, and metal residues of these precious catalysts are problems in the silicone industry. Thus, a strong interest in more sustainable catalysts and for more economic processes exists. Read More

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January 2021

Cross-Dehydrogenative Alkynylation: A Powerful Tool for the Synthesis of Internal Alkynes.

ChemSusChem 2020 Sep 13;13(18):4776-4794. Epub 2020 Aug 13.

Division of Chemistry, Faculty of Pure and Applied Sciences, University of Tsukuba, Tsukuba, Ibaraki, 3058571, Japan.

Alkynes are among the most fundamentally important organic compounds and are widely used in synthetic chemistry, biochemistry, and materials science. Thus, the development of an efficient and sustainable method for the preparation of alkynes has been a central concern in organic synthesis. Cross-dehydrogenative coupling utilizing E-H and Z-H bonds in two different molecules can avoid the need for prefunctionalization of starting materials and has become one of the most straightforward methods for the construction of E-Z chemical bonds. Read More

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September 2020

Polyphenylene-Based Solid Acid as an Efficient Catalyst for Activation and Hydration of Alkynes.

Chem Mater 2020 May 1;32(10):4375-4382. Epub 2020 May 1.

Department of Chemical Engineering, University College London, Torrington Place, London WC1E 7JE, U.K.

Porous polymer catalysts possess the potential to combine the advantages of heterogeneous and homogeneous catalysis, namely, easy postreaction recycling and high dispersion of active sites. Here, we designed a -SOH functionalized polyphenylene (PPhen) framework with purely sp-hybridized carbons, which exhibited high activity in the hydration of alkynes including challenging aliphatic substrates such as 1-octyne. The superiority of the structure lies in its covalent crosslink in the -plane with a π-π stacking interaction between the planes, enabling simultaneously high swellability and porosity (653 m·g). Read More

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Designing Homogeneous Copper-Free Sonogashira Reaction through a Prism of Pd-Pd Transmetalation.

Org Lett 2020 Jul 7;22(13):4938-4943. Epub 2020 May 7.

Faculty of Chemistry and Chemical Technology, University of Ljubljana, Večna pot 113, SI-1000 Ljubljana, Slovenia.

Simultaneous introduction of two different palladium (pre)catalysts, one tuned to promote oxidative addition to (hetero)aryl bromide and another to activate terminal alkyne substrate, leads to productive Pd-Pd transmetalation, subsequent reductive elimination, and formation of disubstituted alkyne. This conceptually novel rational design of copper-free Sonogashira reaction enabled facile identification of the reaction conditions, suitable for the synthesis of alkyl, aryl, and heteroaryl substituted alkynes at room temperature with as low as 0.125 mol % total Pd loading. Read More

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Synthesis of All-Carbon Disubstituted Bicyclo[1.1.1]pentanes by Iron-Catalyzed Kumada Cross-Coupling.

Angew Chem Int Ed Engl 2020 07 14;59(29):11866-11870. Epub 2020 May 14.

Chemistry Research Laboratory, University of Oxford, 12 Mansfield Road, Oxford, OX1 3TA, UK.

1,3-Disubstituted bicyclo[1.1.1]pentanes (BCPs) are important motifs in drug design as surrogates for p-substituted arenes and alkynes. Read More

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A Highly Efficient Dimeric Manganese-Catalyzed Selective Hydroarylation of Internal Alkynes.

Angew Chem Int Ed Engl 2020 Jul 25;59(31):12789-12794. Epub 2020 May 25.

State Key Laboratory of Coordination Chemistry, Jiangsu Key Laboratory of Advanced Organic Materials, Chemistry and Biomedicine Innovation Center (ChemBIC), School of Chemistry and Chemical Engineering, Nanjing University, Nanjing, 210023, China.

We have developed a general and site-predictable manganese-catalyzed hydroarylation of internal alkynes in the presence of water, under an air atmosphere without the involvement of ligand. The unique catalytic feature of this reaction is highlighted by comparison with other widely used transition metal catalysts including palladium, rhodium, nickel, or copper. The simple operation, high efficiency and excellent functional group compatibility make this protocol practical for more than 90 structurally diverse internal alkynes, overcoming the influence of both electronic and steric effect of alkynes. Read More

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Small Gold(I) and Gold(I)-Silver(I) Clusters by C-Si Auration.

Chemistry 2020 Jun 11;26(32):7309-7313. Epub 2020 May 11.

Institute of Chemical Research of Catalonia (ICIQ), Barcelona Institute of Science and Technology, Av. Països Catalans 16, 43007, Tarragona, Spain.

Auration of o-trimethylsilyl arylphosphines leads to the formation of gold and gold-silver clusters with ortho-metalated phosphines displaying 3c-2e Au-C-M bonds (M=Au/Ag). Hexagold clusters [Au L ](X) are obtained by reaction of (L-TMS)AuCl with AgX, whereas reaction with AgX and Ag O leads to gold-silver clusters [Au Ag L ](X) . Oxo-trigold(I) species [Au O] were identified as the intermediates in the formation of the silver-doped clusters. Read More

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Diastereo- and Enantioselective 1,4-Difunctionalization of Borylenynes by Catalytic Conjunctive Cross-Coupling.

Angew Chem Int Ed Engl 2020 06 15;59(26):10311-10315. Epub 2020 Apr 15.

Department of Chemistry, Boston College, 2609 Beacon Street, Chestnut Hill, MA, 02467, USA.

Enantioselective conjunctive cross-coupling of enyne-derived boronate complexes occurs with 1,4 addition of the electrophile and migrating group across the π system. This reaction pathway furnishes α-boryl allenes as the reaction product. In the presence of a chiral catalyst, both the central and axial chirality of the product can be controlled during product formation. Read More

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Samarium(II) Monoalkyl Complex Supported by a β-Diketiminato-Based Tetradentate Ligand: Synthesis, Structure, and Catalytic Hydrosilylation of Internal Alkynes.

Chemistry 2020 Apr 15;26(24):5494-5499. Epub 2020 Apr 15.

State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, 345 Lingling Road, Shanghai, 200032, P. R. China.

The synthesis and catalytic applications of trivalent rare-earth metal alkyl complexes have been well developed, but the chemistry of divalent rare-earth metal alkyl complexes lagged much behind. Herein, we report the synthesis, structure, and catalytic applications of a samarium(II) monoalkyl complex supported by a β-diketiminato-based tetradentate ligand, [LSmCH(SiMe ) ] (L=[MeC(NDipp)CHC(Me)NCH CH N(Me)CH CH NMe ] , Dipp=2,6-(iPr) C H ). This complex is synthesized by the salt metathesis reaction of samarium iodide [LSm(μ-I)] and KCH(SiMe ) in 63 % yield. Read More

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Release kinetics of fluorescent dyes from PLGA nanoparticles in retinal blood vessels: In vivo monitoring and ex vivo localization.

Eur J Pharm Biopharm 2020 May 6;150:131-142. Epub 2020 Mar 6.

Institute of Medical Psychology, Medical Faculty, Otto-von-Guericke University Magdeburg, Leipziger Str. 44, 39120 Magdeburg, Germany; Clinic of Neurology with Institute of Translational Neurology, University Clinic Muenster, Mendel Str. 7, 49148 Muenster, Germany.

PLGA (poly(lactic-co-glycolic acid))-based nanoparticles (NPs) are promising drug carrier systems because of their excellent biocompatibility and ability for sustained drug release. However, it is not well understood how the kinetics of such drug delivery system perform in the retinal blood circulation as imaged in vivo and in real time. To answer this question, PLGA NPs were loaded either with lipophilic carbocyanine perchlorate (DiI) or hydrophilic Rhodamine 123 (Rho123) and coated with poloxamer 188 (P188): PLGA-DiI/P188 and PLGA-Rho123/P188. Read More

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Silver-Catalyzed Activation of Terminal Alkynes for Synthesizing Nitrogen-Containing Molecules.

Acc Chem Res 2020 03 20;53(3):662-675. Epub 2020 Feb 20.

Jilin Province Key Laboratory of Organic Functional Molecular Design & Synthesis, Department of Chemistry, Northeast Normal University, Changchun 130024, China.

Alkynes are one of the most abundant chemicals in organic chemistry, and therefore the development of catalytic reactions to transform alkynes into other useful functionalities is of great value. In recent decades, extraordinary advances have been made in this area with transition-metal catalysis, and silver-based reagents are ideal for the activation of alkynes. This high reactivity is probably due to the superior π-Lewis acidic, carbophilic behavior of silver(I), allowing it to selectively activate carbon-carbon triple bonds (C≡C) through the formation of a silver-π complex. Read More

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Transposing Lateral Flow Immunoassays to Capillary-Driven Microfluidics Using Self-Coalescence Modules and Capillary-Assembled Receptor Carriers.

Anal Chem 2020 01 20;92(1):940-946. Epub 2019 Dec 20.

IBM Research - Zurich , 8803 Rüschlikon , Switzerland.

Point-of-care (POC) immunodiagnostic tests play a crucial role in enabling rapid and correct diagnosis of diseases in prehospital care, emergency, and remote settings. In this work, we present a silicon-based, capillary-driven microfluidic chip integrating two microfluidic modules for the implementation of highly miniaturized immunoassays. Specifically, we apply state-of-the-art microfluidic technology to demonstrate a one-step immunoassay for the detection of the cardiac marker troponin I in human serum using sample volumes of ∼1 μL and with a limit of detection (LOD) of ∼4 ng mL within 25 min. Read More

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January 2020

Metalla-electrocatalyzed C-H Activation by Earth-Abundant 3d Metals and Beyond.

Lutz Ackermann

Acc Chem Res 2020 Jan 19;53(1):84-104. Epub 2019 Dec 19.

Institut für Organische und Biomolekulare Chemie , Georg-August-Universität , Tammannstrasse 2 , 37077 Göttingen , Germany.

To improve the efficacy of molecular syntheses, researchers wish to capitalize upon the selective modification of otherwise inert C-H bonds. The past two decades have witnessed considerable advances in coordination chemistry that have set the stage for transformative tools for C-H functionalizations. Particularly, oxidative C-H/C-H and C-H/Het-H transformations have gained major attention because they avoid all elements of substrate prefunctionalization. Read More

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January 2020

Asymmetric Synthesis of a Fused Tricyclic Hydronaphthofuran Scaffold by Desymmetric [2+2+2] Cycloaddition.

Angew Chem Int Ed Engl 2020 Feb 30;59(6):2220-2224. Epub 2019 Dec 30.

Key Lab for Colloid and Interface Chemistry of Education Ministry, Department of Chemistry, Shandong University, No. 27 South Shanda Road, Jinan, 250100, China.

A rhodium(I)-BINAP-catalyzed highly enantioselective [2+2+2] cycloaddition of enynes with alkynes has been developed. Diverse fused tricyclic hydronaphthofuran scaffolds with three consecutive stereogenic centers were constructed in one step from easily available materials with excellent chemo-, regio-, diastereo-, and enantioselectivity. Notable features of these reactions include 100 % atom economy, very broad scope, and mild reaction conditions. Read More

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February 2020