Publications by authors named "Yanghui Zhang"

53 Publications

Synthesis of 9-Fluorenylidenes via Pd-Catalyzed C-H Vinylation with Vinyl Bromides.

Org Lett 2021 Oct 24;23(20):7746-7750. Epub 2021 Sep 24.

School of Chemical Science and Engineering, Shanghai Key Laboratory of Chemical Assessment and Sustainability, Tongji University 1239 Siping Road, Shanghai 200092, China.

A facile and efficient approach for the synthesis of 9-fluorenylidenes has been developed via the palladium-catalyzed cross-coupling of 2-iodobiphenyls and vinyl bromides. The reaction involves the C-H activation of 2-iodobiphenyls and dual C-C bond formations. A range of 9-fluorenylidene derivatives, including diphenyldibenzofulvenes, can be synthesized with the reaction.
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http://dx.doi.org/10.1021/acs.orglett.1c02722DOI Listing
October 2021

Intermolecular C-H silylation through cascade carbopalladation and vinylic to aryl 1,4-palladium migration.

Chem Commun (Camb) 2021 Sep 23;57(76):9700-9703. Epub 2021 Sep 23.

School of Chemical Science and Engineering, Shanghai Key Laboratory of Chemical Assessment and Sustainability, Tongji University, 1239 Siping Road, Shanghai 200092, China.

A palladium-catalyzed remote C-H silylation reaction has been developed through vinylic to aryl 1,4-palladium migration. By using alkyne-tethered aryl iodides as the starting materials and hexamethyldisilane as the silylating reagent, the reaction involves cascade intramolecular carbopalladation, 1,4-palladium migration, and silylation with hexamethyldisilane, and leads to the formation of exocyclic alkene-containing 5-silylisoquinolines as the final products.
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http://dx.doi.org/10.1039/d1cc03677gDOI Listing
September 2021

Palladium-Catalyzed Intramolecular Cross-Coupling of Unactivated C(sp)-H and C(sp)-H Bonds.

Org Lett 2021 Sep 3;23(18):7161-7165. Epub 2021 Sep 3.

School of Chemical Science and Engineering, Shanghai Key Laboratory of Chemical Assessment and Sustainability, Tongji University, 1239 Siping Road, Shanghai 200092, China.

Direct C-H/C-H coupling represents an appealing method for the construction of C-C bonds, and the cross-coupling of unactivated C(sp)-H and C(sp)-H bonds is challenging and remains to be investigated. We have developed the Pd-catalyzed intramolecular coupling of inert C(sp)-H and C(sp)-H bonds. The reaction proceeded by -methyl oxime-directed aryl C(sp)-H activation and subsequent alkyl C(sp)-H cleavage, generating C(sp),C(sp)-palladacycles as the key intermediates. Dihydrobenzofurans and indanes were formed as the final products.
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http://dx.doi.org/10.1021/acs.orglett.1c02567DOI Listing
September 2021

Bivalirudin versus unfractionated heparin during percutaneous coronary intervention in high-bleeding-risk patients with acute coronary syndrome in contemporary practice.

Biomed Pharmacother 2020 Oct 17;130:110758. Epub 2020 Sep 17.

Department of Cardiology, The First Affiliated Hospital of Zhengzhou University, Zhengzhou, Henan, China. Electronic address:

Background: Bivalirudin, as compared with unfractionated heparin (UFH), has been shown to reduce bleeding complications and supply a better safety profile among low/medium-bleeding-risk patients undergoing percutaneous coronary intervention (PCI) for acute coronary syndrome (ACS) in some previous studies. Whether this advantage persists in patients at high risk of bleeding according to contemporary practice characterized by frequent use of radial-artery access and novel P2Y inhibitors, and low use of glycoprotein IIb/IIIa inhibitors (GPIs) is unclear.

Aim Of The Study: This study aimed to assess the efficacy and safety of bivalirudin compared with UFH in high bleeding risk patients with ACS undergoing PCI in current practice.

Materials And Methods: All consecutive high-bleeding-risk patients who underwent PCI for ACS at the First Affiliated Hospital of Zhengzhou University from January to September 2019 were retrospectively analyzed. The 30-day primary outcome was a composite of major bleeding, myocardial infarction, all-cause death, or stroke (net adverse clinical events [NACEs]), and the secondary outcomes at 30 days included a composite of myocardial infarction, stoke, or all-cause death (major adverse cardiovascular events [MACEs]), each component of the primary outcome, target vessel revascularization (TVR) and stent thrombosis (ST). Besides, we assessed angina-related health status at 30 days, the length of hospital stay, and hospitalization costs. A logistic regression model was used to adjust for baseline differences. Consistency of the treatment effect of bivalirudin for NACEs and MACEs compared with UFH was evaluated in 15 prespecified subgroups.

Results: From January to September 2019, 823 patients (361 treated with bivalirudin and 462 treated with UFH) were enrolled in the study. GPIs, novel P2Y inhibitors, and radial approach was used in 5.6 %, 66.1 %, and 89.7 % of the patients, respectively. After adjusting for baseline differences, bivalirudin was associated with significant reduction in NACEs, MACEs, major bleeding, and myocardial infarction at 30 days compared with UFH. The individual endpoints of death, stroke, ST and TVR did not differ significantly between the 2 groups after adjusting for covariates. Furthermore, bivalirudin consistently reduced the rates of NACEs and MACEs in the 15 prespecified subgroups compared with UFH. These benefits of bivalirudin can translate into improved angina-related health status, shorter hospital stays, and lower hospitalization costs.

Conclusions: The treatment of bivalirudin showed better efficacy and safety as compared to UFH among patients with ACS undergoing PCI at high risk of bleeding in contemporary practice.
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http://dx.doi.org/10.1016/j.biopha.2020.110758DOI Listing
October 2020

Palladium-Catalyzed -Carbosilylation of Alkynes to Access Isoquinolinone-Containing Exocyclic Vinylsilanes.

Org Lett 2021 Aug 14;23(15):5772-5776. Epub 2021 Jul 14.

School of Chemical Science and Engineering, Shanghai Key Laboratory of Chemical Assessment and Sustainability, Tongji University 1239 Siping Road, Shanghai 200092, China.

A Pd-catalyzed -selective carbosilylation reaction of alkynes has been developed. The -vinylpalladium species, generated through intramolecular -carbopalladation of alkynes and subsequent - isomerization, were captured by hexamethyldisilane to form multisubstituted vinylsilanes. This reaction provides a useful strategy for the stereoselective synthesis of isoquinolinone-containing exocyclic tetrasubstituted vinylsilanes.
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http://dx.doi.org/10.1021/acs.orglett.1c01931DOI Listing
August 2021

Pd-catalyzed cross-electrophile Coupling/C-H alkylation reaction enabled by a mediator generated C(sp)-H activation.

Chem Sci 2021 May 19;12(24):8531-8536. Epub 2021 May 19.

School of Chemical Science and Engineering, Shanghai Key Laboratory of Chemical Assessment and Sustainability, Tongji University 1239 Siping Road Shanghai 200092 China

Transition-metal-catalyzed cross-electrophile C(sp)-(sp) coupling and C-H alkylation reactions represent two efficient methods for the incorporation of an alkyl group into aromatic rings. Herein, we report a Pd-catalyzed cascade cross-electrophile coupling and C-H alkylation reaction of 2-iodo-alkoxylarenes with alkyl chlorides. Methoxy and benzyloxy groups, which are ubiquitous functional groups and common protecting groups, were utilized as crucial mediators primary or secondary C(sp)-H activation. The reaction provides an innovative and convenient access for the synthesis of alkylated phenol derivatives, which are widely found in bioactive compounds and organic functional materials.
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http://dx.doi.org/10.1039/d1sc01731dDOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC8221197PMC
May 2021

Efficacy and Safety of Bivalirudin During Percutaneous Coronary Intervention in Chronic Total Occlusion: A Retrospective Study.

Clin Ther 2021 05 31;43(5):844-851. Epub 2021 Mar 31.

Department of Cardiology, the First Affiliated Hospital of Zhengzhou University, Zhengzhou, Henan, China. Electronic address:

Purpose: Bivalirudin as a thrombin inhibitor is proven to have a low risk of bleeding during percutaneous coronary intervention (PCI). Some evidence indicates comparable effectiveness and safety between bivalirudin and unfractionated heparin (UFH). Although bivalirudin during PCI offers more clinical and safety benefits to patients with chronic total occlusion (CTO), mostly via radial access, this has not been confirmed. The objective of this study was to examine the efficacy and safety of bivalirudin during percutaneous coronary intervention (PCI) in patients with CTO.

Methods: This trial used a retrospective cohort study design. Medical information from 736 patients with CTO who underwent PCI with bivalirudin or UFH at the First Affiliated Hospital of Zhengzhou University from July 2019 to September 2020 was extracted and analyzed. The primary end point was the 30-day incidence of net adverse clinical events (NACEs), and the secondary end point was the major adverse cardiovascular events (MACEs), which were related to safety and efficacy, respectively. Other end points incorporated each component of the primary outcome, target vessel revascularization, and stent thrombosis. Clinical and procedural characteristics at baseline were adjusted by using a logistic regression model.

Findings: Overall, 71.5% of patients with CTO used the radial approach. Both groups exhibited nonsignificant differences in the majority of baseline characteristics. The bivalirudin group was associated with a significant reduction in NACEs (12.9% vs 21.5%; P = 0.002) and major bleeding (2.5% vs 8.0%; P = 0.001) versus the UFH group at the end of the 30-day follow-up. The incidence of MACEs, myocardial infarction, death, stroke, stent thrombosis, and target vessel revascularization did not differ significantly between the 2 groups. Moreover, the bivalirudin group also reported a lower incidence of NACEs in the prespecified subgroups.

Implications: Bivalirudin exhibited comparative efficacy but superior safety compared with UFH among patients with CTO undergoing PCI. Chinese Clinical Trial Registry: ChiCTR2000034771.
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http://dx.doi.org/10.1016/j.clinthera.2021.03.004DOI Listing
May 2021

Pd-Catalyzed ,-Dimethylation of -Substituted Iodoarenes via a Base-Controlled C-H Activation Cascade with Dimethyl Carbonate as the Methyl Source.

J Am Chem Soc 2021 03 22;143(12):4524-4530. Epub 2021 Mar 22.

School of Chemical Science and Engineering, Shanghai Key Laboratory of Chemical Assessment and Sustainability, Tongji University, 1239 Siping Road, Shanghai 200092, China.

A methyl group can have a profound impact on the pharmacological properties of organic molecules. Hence, developing methylation methods and methylating reagents is essential in medicinal chemistry. We report a palladium-catalyzed dimethylation reaction of -substituted iodoarenes using dimethyl carbonate as a methyl source. In the presence of KCO as a base, iodoarenes are dimethylated at the - and -positions of the iodo group, which represents a novel strategy for -C-H methylation. With KOAc as the base, subsequent oxidative C(sp)-H/C(sp)-H coupling occurs; in this case, the overall transformation achieves triple C-H activation to form three new C-C bonds. These reactions allow expedient access to 2,6-dimethylated phenols, 2,3-dihydrobenzofurans, and indanes, which are ubiquitous structural motifs and essential synthetic intermediates of biologically and pharmacologically active compounds.
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http://dx.doi.org/10.1021/jacs.0c13057DOI Listing
March 2021

Palladium-catalyzed diastereoselective cross-coupling of two aryl halides C-H activation: synthesis of chiral eight-membered nitrogen heterocycles.

Chem Commun (Camb) 2021 Mar;57(23):2939-2942

School of Chemical Science and Engineering, Shanghai Key Laboratory of Chemical Assessment and Sustainability, Tongji University, 1239 Siping Road, Shanghai 200092, China.

A method for the synthesis of enantiopure eight-membered nitrogen heterocycles has been developed through diastereoselective cross-coupling of 2-iodobiphenyls with 2-bromobenzylamines. The products represent a novel type of chiral scaffold, which feature easy modification and high configurative stability and have the potential to be applied in asymmetric synthesis. Palladacycles that were formed via the C-H activation of 2-iodobiphenyls should act as the intermediates. The reaction provides a new strategy for the synthesis of medium-sized ring compounds.
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http://dx.doi.org/10.1039/d1cc00398dDOI Listing
March 2021

Diastereoselective Construction of Eight-Membered Carbocycles through Palladium-Catalyzed C(sp)-H Functionalization.

Org Lett 2021 Feb 9;23(4):1269-1274. Epub 2021 Feb 9.

School of Chemical Science and Engineering, Shanghai Key Laboratory of Chemical Assessment and Sustainability, Tongji University, 1239 Siping Road, Shanghai, 200092, P. R. China.

A palladium-catalyzed cross-coupling reaction of 2-alkylphenyl bromides with biphenylene has been developed. The reactions formed eight-membered carbocycles through C(sp)-H activation and the formation of two C-C bonds, and the chiral products were obtained with excellent diastereoselectivity. The reaction provides a new strategy for the construction of eight-membered carbocycles, and the products represent a novel type of chiral scaffold.
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http://dx.doi.org/10.1021/acs.orglett.0c04244DOI Listing
February 2021

Palladium-Catalyzed Dual Coupling Reaction of 2-Iodobiphenyls with -Bromoanilines through C-H Activation: An Approach for the Synthesis of Tribenzo[,,]azepines.

Org Lett 2021 Feb 8;23(4):1239-1242. Epub 2021 Feb 8.

School of Chemical Science and Engineering, Shanghai Key Laboratory of Chemical Assessment and Sustainability, Tongji University, 1239 Siping Road, Shanghai 200092, China.

A novel and straightforward approach for the synthesis of tribenzo[,,]azepines starting from 2-iodobiphenyls and 2-bromoanilines has been developed. A wide range of tribenzo[,,]azepines were obtained in good to excellent yields via a cascade intermolecular palladium-catalyzed C-H activation/dual coupling reaction. ,-palladacycles, which are generated by C-H activation of 2-iodobiphenyls, should be the reaction intermediates.
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http://dx.doi.org/10.1021/acs.orglett.0c04192DOI Listing
February 2021

C(sp)-H activation-enabled cross-coupling of two aryl halides: an approach to 9,10-dihydrophenanthrenes.

Chem Commun (Camb) 2020 Sep;56(74):10942-10945

School of Chemical Science and Engineering, Shanghai Key Laboratory of Chemical Assessment and Sustainability, Tongji University, 1239 Siping Road, Shanghai 200092, China.

A palladium-catalyzed cross-coupling reaction of aryl halides with 2-chlorobenzoic acids has been developed. The reaction forms C(sp3), C(sp2)-palladacycles through C(sp3)-H activation. The palladacycles react with 2-chlorobenzoic acids through two successive C-C cross-couplings, and two C-C bonds are formed with high chemoselectivity. The reaction provides an innovative method for the synthesis of 9,10-dihydrophenanthrenes.
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http://dx.doi.org/10.1039/d0cc04602gDOI Listing
September 2020

Synthesis of 3,4-Fused Tricyclic Indoles through Cascade Carbopalladation and C-H Amination: Development and Total Synthesis of Rucaparib.

Org Lett 2020 07 17;22(13):4985-4989. Epub 2020 Jun 17.

School of Chemical Science and Engineering, Shanghai Key Laboratory of Chemical Assessment and Sustainability, Tongji University 1239 Siping Road, Shanghai 200092, China.

3,4-Fused tricyclic indole scaffolds are ubiquitous in bioactive natural products and pharmaceuticals. A new protocol for the synthesis of 3,4-fused tricyclic indoles has been developed through cascade carbopalladation and C-H amination with ,-di--butyldiaziridinone. The protocol allows access to a range of 3,4-fused tricyclic indoles, including those containing various linkers and fused with medium-sized rings. Rucaparib can be synthesized via this reaction, providing an advantageous synthetic method for the FDA-approved cancer medicine.
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http://dx.doi.org/10.1021/acs.orglett.0c01513DOI Listing
July 2020

Palladium-catalyzed intermolecular C-H silylation initiated by aminopalladation.

Chem Commun (Camb) 2020 Jul;56(56):7801-7804

School of Chemical Science and Engineering, Shanghai Key Laboratory of Chemical Assessment and Sustainability, Tongji University, 1239 Siping Road, Shanghai, 200092, P. R. China.

A Pd(ii)-catalyzed intermolecular C-H silylation reaction initiated by aminopalladation has been developed. The C-H bonds were activated by an alkyl Pd(ii) species generated through aminopalladation and then disilylated with hexamethyldisilane to form disilylated indolines as the final products. The reaction provides a new method for the introduction of silyl groups into complex organic molecules.
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http://dx.doi.org/10.1039/d0cc00872aDOI Listing
July 2020

Enantioselective synthesis of quaternary 3,4-dihydroisoquinolinones Heck carbonylation reactions: development and application to the synthesis of Minalrestat analogues.

Chem Sci 2019 Nov 3;10(42):9853-9858. Epub 2019 Sep 3.

School of Chemical Science and Engineering , Shanghai Key Laboratory of Chemical Assessment and Sustainability , Tongji University , 1239 Siping Road , Shanghai 200092 , China . Email:

Minalrestat and its analogues represent structurally novel aldose reductase inhibitors, and the asymmetric synthesis of such pharmaceutically privileged molecules has not been reported yet. We have developed a palladium-catalyzed enantioselective intramolecular carbonylative Heck reaction by using formate esters as the source of CO, which represents the first enantioselective synthesis of quaternary 3,4-dihydroisoquinolines. The reaction provides a facile and efficient method for the synthesis of enantiopure nitrogen-containing heterocyclic compounds bearing an all-carbon quaternary stereocenter. The reaction has been successfully applied to the first asymmetric synthesis of Minalrestat analogues.
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http://dx.doi.org/10.1039/c9sc03406dDOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC6977551PMC
November 2019

GTX.Digest.VCF: an online NGS data interpretation system based on intelligent gene ranking and large-scale text mining.

BMC Med Genomics 2019 12 20;12(Suppl 8):193. Epub 2019 Dec 20.

Genetalks Biotech. Co., Ltd., Changsha, 410000, China.

Background: An important task in the interpretation of sequencing data is to highlight pathogenic genes (or detrimental variants) in the field of Mendelian diseases. It is still challenging despite the recent rapid development of genomics and bioinformatics. A typical interpretation workflow includes annotation, filtration, manual inspection and literature review. Those steps are time-consuming and error-prone in the absence of systematic support. Therefore, we developed GTX.Digest.VCF, an online DNA sequencing interpretation system, which prioritizes genes and variants for novel disease-gene relation discovery and integrates text mining results to provide literature evidence for the discovery. Its phenotype-driven ranking and biological data mining approach significantly speed up the whole interpretation process.

Results: The GTX.Digest.VCF system is freely available as a web portal at http://vcf.gtxlab.com for academic research. Evaluation on the DDD project dataset demonstrates an accuracy of 77% (235 out of 305 cases) for top-50 genes and an accuracy of 41.6% (127 out of 305 cases) for top-5 genes.

Conclusions: GTX.Digest.VCF provides an intelligent web portal for genomics data interpretation via the integration of bioinformatics tools, distributed parallel computing, biomedical text mining. It can facilitate the application of genomic analytics in clinical research and practices.
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http://dx.doi.org/10.1186/s12920-019-0637-xDOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC6923899PMC
December 2019

A De Novo Variant Identified in the PPP2R1A Gene in an Infant Induces Neurodevelopmental Abnormalities.

Neurosci Bull 2020 Feb 17;36(2):179-182. Epub 2019 Sep 17.

National Health Commission Key Laboratory of Birth Defects Research, Prevention and Treatment, Hunan Provincial Maternal and Child Health Care Hospital, Changsha, 410008, China.

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http://dx.doi.org/10.1007/s12264-019-00430-4DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC6977796PMC
February 2020

The first case of a non-infertile female patient with Pitt-Hopkins syndrome.

Am J Med Genet A 2019 11 28;179(11):2311-2314. Epub 2019 Aug 28.

Department of Medical Genetics, Hunan Provincial Maternal and Child Health Care Hospital, Changsha, Hunan, China.

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http://dx.doi.org/10.1002/ajmg.a.61325DOI Listing
November 2019

Synthesis of Indolines by Palladium-Catalyzed Intermolecular Amination of Unactivated C(sp)-H Bonds.

Org Lett 2019 08 5;21(16):6508-6512. Epub 2019 Aug 5.

School of Chemical Science and Engineering, Shanghai Key Laboratory of Chemical Assessment and Sustainability , Tongji University , 1239 Siping Road , Shanghai , 200092 , P. R. China.

A new palladium-catalyzed C(sp)-H amination reaction has been developed. 1-(-Butyl)-2-iodobenzene and its derivatives undergo palladium-catalyzed C-H activation to form palladacycles. The palladacycles are aminated with diaziridinone to form indolines as the final products. The reaction represents a new method for the synthesis of 3,3-disubstituted indolines, which are essential structural motifs in many bioactive compounds and pharmaceutical targets.
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http://dx.doi.org/10.1021/acs.orglett.9b02386DOI Listing
August 2019

Molecular investigation in Chinese patients with primary carnitine deficiency.

Mol Genet Genomic Med 2019 09 30;7(9):e901. Epub 2019 Jul 30.

Hunan Provincial Maternal and Child Health Care Hospital, Changsha, Hunan, China.

Background: Primary carnitine deficiency (PCD) is an autosomal recessive disorder of carnitine transportation caused by mutations in the SLC22A5 that lead to low serum carnitine levels and decreased intracellular carnitine accumulation. Characteristic clinical findings are hypoketotic hypoglycemia and skeletal and cardiac myopathy.

Objective: To genetically diagnose 24 unrelated Chinese patients with PCD, including 18 infants and six adults.

Methods: The entire coding region and the intron-exon boundaries of SLC22A5 were amplified by polymerase chain reaction (PCR). In silico analyses and reverse transcription-polymerase chain reaction (RT-PCR) were used to predict variants' impact on protein structure and function.

Results: Disease-causing variants in the SLC22A5 were identified in all 24 subjects, and c.288delG, c.495C>A, c.774_775insTCG, c.824+1G>A, and c.1418G>T were novel. The novel variant c.824+1G>A caused a truncated protein p.Phe276Tyrfs*8.

Conclusions: We identified 13 variants in the SLC22A5 in 24 PCD patients, and five of these variants are novel mutations. c.824+1G>A was confirmed to alter mRNA splicing by reverse transcription PCR. Furthermore, our findings broaden the mutation spectrum of SLC22A5 and the understanding of the diverse and variable effects of PCD variants.
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http://dx.doi.org/10.1002/mgg3.901DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC6732302PMC
September 2019

Novel SASS6 compound heterozygous mutations in a Chinese family with primary autosomal recessive microcephaly.

Clin Chim Acta 2019 Apr 10;491:15-18. Epub 2019 Jan 10.

Hunan Provincial Maternal and Child Health Care Hospital, NO.53 Xiangchun Road, Changsha, Hunan 410008, China; NHC Key Laboratory of Birth Defects Research, Prevention and Treatment (Hunan Provincial Maternal and Child Health Care Hospital), NO.53 Xiangchun Road, Changsha, Hunan 410008, China. Electronic address:

Primary autosomal recessive microcephaly (MCPH) is a rare hereditary disease characterized by congenitally small with brain circumference of the head below 3 standard deviations (SD). By far, 18 MCPH genes have been reported to be associated with the disease. SASS6 gene functioned in assembly of centrioles that the majority of MCPH genes present at the centrosome. There was only research reporting a homozygous missense mutation in SASS6 gene detected in a consanguineous Pakistani family. By conducting Whole-exome sequencing (WES) and Sanger sequencing on the family trio, we identified two novel splice site mutations c.127-13A>G and c.1867+2T>A in compound heterozygous hereditary form in the SASS6 gene. The two mutations were confirmed to alter mRNA splicing by RT-PCR assay. Our finding supported the role of SASS6 in the pathogenesis of microcephaly, expanding mutation spectrums and contributing to understanding of molecular mechanisms of MCPH.
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http://dx.doi.org/10.1016/j.cca.2019.01.007DOI Listing
April 2019

Synthesis of Indoles through Palladium-Catalyzed Three-Component Reaction of Aryl Iodides, Alkynes, and Diaziridinone.

Org Lett 2018 10 10;20(20):6440-6443. Epub 2018 Oct 10.

School of Chemical Science and Engineering, Shanghai Key Laboratory of Chemical Assessment and Sustainability , Tongji University , 1239 Siping Road , Shanghai , 200092 , P. R. China.

The three-component reaction of aryl iodides, alkynes, and diaziridinone is described. The reaction provides an innovative synthetic approach for indoles. The approach features high efficiency, broad substrate scope, and excellent regioselectivity. C, C-Palladacycles should act as the intermediates. The C, C-palladacycles are obtained from simple aryl halides and alkynes and then reacted with diaziridinone to afford indoles.
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http://dx.doi.org/10.1021/acs.orglett.8b02750DOI Listing
October 2018

Palladium-catalyzed sequential three-component reactions to access vinylsilanes.

Chem Commun (Camb) 2018 Sep 3;54(75):10598-10601. Epub 2018 Sep 3.

School of Chemical Science and Engineering, Shanghai Key Laboratory of Chemical, Assessment and Sustainability, Tongji University, 1239 Siping Road, Shanghai, 200092, P. R. China.

A palladium-catalyzed sequential three-component reaction has been developed. The palladacycles, generated through cascade reactions of aryl halides and alkynes, are the key intermediates and react with hexamethyldisilane to form disilylated products. The reaction represents a useful preparative method for vinylsilanes, and the vinylsilanes can be transformed into tetrasubstituted alkenes.
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http://dx.doi.org/10.1039/c8cc05254aDOI Listing
September 2018

Palladium-Catalyzed C-H Silylation through Palladacycles Generated from Aryl Halides.

Angew Chem Int Ed Engl 2018 03 19;57(12):3233-3237. Epub 2018 Feb 19.

School of Chemical Science and Engineering, Shanghai Key Laboratory of Chemical Assessment and Sustainability, Tongji University, 1239 Siping Road, Shanghai, 200092, China.

A highly efficient palladium-catalyzed disilylation reaction of aryl halides through C-H activation has been developed for the first time. The reaction has broad substrate scope. A variety of aryl halides can be disilylated by three types of C-H activation, including C(sp )-H, C(sp )-H, and remote C-H activation. In particular, the reactions are also unusually efficient. The yields are essentially quantitative in many cases, even in the presence of less than 1 mol % catalyst and 1 equivalent of the silylating reagent under relatively mild conditions. The disilylated biphenyls can be converted into disiloxane-bridged biphenyls.
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http://dx.doi.org/10.1002/anie.201800330DOI Listing
March 2018

Synthesis of 9,9-Disubstituted Fluorenes from 2-Iodobiphenyls and α-Diazoesters under Palladium Catalysis.

J Org Chem 2018 01 8;83(2):1065-1072. Epub 2018 Jan 8.

School of Chemical Science and Engineering, Shanghai Key Laboratory of Chemical Assessment and Sustainability, Tongji University , 1239 Siping Road, Shanghai 200092, P. R. China.

9,9-Disubstituted fluorenes are widely employed in materials science. We have developed a straightforward approach for the synthesis of 9,9-disubstituted fluorenes from 2-iodobiphenyls and α-diazoesters. The reaction proceeds via a tandem palladium-catalyzed C(sp)-H activation/carbenoid insertion sequence.
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http://dx.doi.org/10.1021/acs.joc.7b02885DOI Listing
January 2018

An approach to spirooxindoles via palladium-catalyzed remote C-H activation and dual alkylation with CHBr.

Chem Commun (Camb) 2017 Sep 8;53(75):10429-10432. Epub 2017 Sep 8.

School of Chemical Science and Engineering, Shanghai Key Laboratory of Chemical Assessment and Sustainability, Tongji University, 1239 Siping Road, Shanghai, 200092, P. R. China.

A facile and efficient approach for the synthesis of spirooxindoles has been developed via the coupling of spirocyclic C,C-palladacycles with CHBr. The key spirocyclic palladacycles are generated catalytically via remote C-H activation. A range of spirooxindoles can be synthesized in good to excellent yields from readily available starting material.
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http://dx.doi.org/10.1039/c7cc06196jDOI Listing
September 2017

Palladium-Catalyzed Alkylation with Alkyl Halides by C(sp )-H Activation.

Angew Chem Int Ed Engl 2017 09 24;56(40):12288-12291. Epub 2017 Aug 24.

School of Chemical Science and Engineering, Shanghai Key Laboratory of Chemical Assessment and Sustainability, Tongji University, 1239 Siping Road, Shanghai, 200092, China.

Utilizing halogens as traceless directing goups represents an attractive strategy for C-H functionalization. A two C-H alkylation system, initiated by the oxidative addition of organohalides to Pd , has been developed. The first reaction involves an intermolecular alkylation of palladacycles to form C(sp )-C(sp ) bonds followed by C(sp )-H activation/cyclization to deliver alkylated benzocyclobutenes as the final products. In the second reaction, two C-C bonds are formed by the reaction of palladacycles with CH Br , and provides a facile and efficient method for the synthesis of indanes. The alkylated benzocyclobutene products can be transformed into tricyclic hyrocarbons, and the indane derivatives are essential structural motifs in bioactive and odorant molecules.
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http://dx.doi.org/10.1002/anie.201706418DOI Listing
September 2017

Palladium-catalyzed C-H alkylation of 2-phenylpyridines with alkyl iodides.

Org Biomol Chem 2017 Jul;15(26):5616-5624

School of Chemical Science and Engineering, and Shanghai Key Lab of Chemical Assessment and Sustainability, Tongji University, 1239 Siping Road, Shanghai, 200092, P. R. China.

Palladium-catalyzed C-H alkylation reaction of 2-phenylpyridines with alkyl iodides has been successfully developed. The palladacycles obtained from 2-phenylpyridines should act as the key intermediates in the alkylation reaction.
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http://dx.doi.org/10.1039/c7ob01232bDOI Listing
July 2017

Oxalic acid as the in situ carbon monoxide generator in palladium-catalyzed hydroxycarbonylation of arylhalides.

Org Biomol Chem 2017 Jun;15(23):5033-5040

School of Chemical Science and Engineering, Tongji University, 1239 Siping Road, Shanghai 200092, P.R. China.

An efficient palladium-catalyzed hydroxycarbonylation reaction of arylhalides using oxalic acid as a CO source has been developed. The reaction features high safety, low catalyst loading, and a broad substrate scope, and provides a safe and tractable approach to access a variety of aromatic carboxylic acid compounds. Mechanistic studies revealed the decomposition pattern of oxalic acid.
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http://dx.doi.org/10.1039/c7ob01052dDOI Listing
June 2017

Synthesis of Triphenylenes Starting from 2-Iodobiphenyls and Iodobenzenes via Palladium-Catalyzed Dual C-H Activation and Double C-C Bond Formation.

Org Lett 2016 Oct 7;18(20):5192-5195. Epub 2016 Oct 7.

School of Chemical Science and Engineering, Shanghai Key Laboratory of Chemical Assessment and Sustainability, Tongji University , 1239 Siping Road, Shanghai 200092, China.

A novel and facile approach for the synthesis of triphenylenes has been developed via palladium-catalyzed coupling of 2-iodobiphenyls and iodobenzenes. The reaction involves dual palladium-catalyzed C-H activations and double palladium-catalyzed C-C bond formations. A range of unsymmetrically functionalized triphenylenes can be synthesized with the reaction. The approach features readily available starting materials, high atom- and step-economy, and access to various unsymmetrically functionalized triphenylenes.
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http://dx.doi.org/10.1021/acs.orglett.6b02071DOI Listing
October 2016
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