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A review of enantioselective dual transition metal/photoredox catalysis

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Science China Chemistry 2020年第5期63卷 637-647页

作者： Hong-Hao Zhang Hui Chen Chengjian Zhu Shouyun Yu Jiangsu Key Laboratory of Advanced Organic Materials School of Chemistry and Chemical EngineeringNanjing UniversityNanjing 210023China

transition metal catalysis is one of the most important tools to construct carbon-carbon and carbon-heteroatom bonds in modern organic synthesis. Visible-light photoredox catalysis has recently drawn considerable attention of the scientific community owing to its unique activation modes and significance for the green synthesis. The merger of photoredox catalysis with transition metal catalysts, termed metallaphotoredox catalysis, has become a popular strategy for expanding the synthetic utility of visiblelight photocatalysis. This strategy has led to the discovery of novel asymmetric transformations, which are unfeasible or not easily accessible by a single catalytic system. This contemporary area of organic chemistry holds promise for the development of economical and environmentally friendly methods for the asymmetric synthesis of chiral compounds. In this review, the advances in the enantioselective metallaphotoredox catalysis(EMPC) are summarized.

关键词： transition metal catalysis photoredox catalysis dual catalysis asymmetric catalysis

Elucidating ligand effects in rhodium(Ⅲ)-catalyzed arene-alkene coupling reactions

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Chinese Chemical Letters 2024年第5期35卷 130-134页

作者： Kongchuan Wu Dandan Lu Jianbin Lin Ting-Bin Wen Wei Hao Kai Tan Hui-Jun Zhang Department of Chemistry College of Chemistry and Chemical EngineeringXiamen UniversityXiamen 361005China Beijing National Laboratory for Molecular Sciences CAS Key Laboratory of Molecular Recognition and FunctionInstitute of ChemistryChinese Academy of Sciences(CAS)Beijing 100190China

Rhodium(Ⅲ)-catalyzed C-H couplings of arenes with alkenes are among the most powerful methods for C-C bond formation.For these transformations,subtle manipulation of ancillary ligands can lead to dramatic changes in reactivity and selectivity.However,detailed mechanistic studies concerning the ligand effects are rare.In this study,we investigated the origin of ligand-controlled product-selectivity in rhodium(Ⅲ)-catalyzed C-H couplings of arenes with alkenes,using a series of well-defined[CpXRhⅢ]complexes that feature electronically or sterically distinct Cp^(X)(Cp(η^(5)-C_(5)H_(5)),Cp^(CF3)(η^(5)-C_(5)Me_(4)CF_(3))and Cp^(∗)(η^(5)-C_(5)Me_(5)))ligands.A combination of experimental and theoretical investigations showed that(i)rhodium hydride species containing the electron rich Cp^(∗)ligand can undergo reinsertion of the alkene,thereby allowing rhodium-walking,(ii)rhodium hydride species involving the electron-deficient Cp or Cp^(CF3) ligands prefer reductive elimination rather than alkene insertion.These findings offer valuable insights on future rational catalyst design for selective arene-alkene cross coupling reactions.

关键词： Organometallics transition metal catalysis Arene-alkene coupling β-H elimination Rhodium hydride

Supramolecular Concepts in transition metal catalysis:from Asymmetric catalysis to Green Energy Applications

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Supramolecular Concepts in Transition Metal Catalysis:from A...

Trisubstituted alkenes featuring aryl groups:stereoselective synthetic strategies and applications

中国化学会第28届学术年会

作者： Joost N.H.Reek Homogeneous and Supramolecular catalysis Van ’t Hoff Institute for Molecular SciencesUniversity of Amsterdam

＜正＞The interface between supramolecular chemistry and transition metal catalysis has received surprisingly little attention in contrast to the individual disciplines.It provides,however,novel and elegant strategies... 详细信息

关键词： Supramolecular catalysis transition metal catalysis rhodium hydroformylation green energy applications

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Science China Chemistry 2023年第5期66卷 1261-1287页

作者： Meng-Yao Li Shuyang Zhai Xiao-Mei Nong Ao Gu Jiatong Li Guo-Qiang Lin Yingbin Liu Shanghai Cancer Institute Renji Hospital Affiliated to Shanghai Jiao Tong University School of MedicineShanghai 200127China Shanghai Institute of Organic Chemistry Chinese Academy of SciencesShanghai 200032China School of Basic Medicine and Clinical Pharmacy China Pharmaceutical UniversityNanjing 211198China

In recent years,the synthesis and application of alkenes have attracted increased attention.Triphenylethenes(TriPEs)have lower molecular torsion than tetraphenylethenes(TPEs),which helps to balance the degree of conjugation and the aggregation-induced emission(AIE)effect.The geometry of double bonds has a significant impact on luminescence.Therefore,it is essential to provide a comprehensive summary of the stereoselective synthetic strategies for trisubstituted alkenes.In this review,common strategies for the stereoselective synthesis of alkenes are described,with an emphasis on the origin of stereoselectivity and the types of substrates.In addition,the AIE properties of TriPE and its applications in optoelectronic devices,stimuli-responsive materials,sensors,and therapies were discussed.

关键词： trisubstituted alkenes stereoselective synthesis aggregation-induced emission transition metal catalysis

transition metal-catalyzed conversion of aldehydes to ketones

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Chinese Chemical Letters 2022年第3期33卷 1207-1226页

作者： Zijuan Yan Pan-Lin Shao Qing Qiang Feipeng Liu Xuchao Wang Yongjie Li Zi-Qiang Rong Frontiers Science Center for Flexible Electronics(FSCFE) Shaanxi Institute of Flexible Electronics(SIFE)&Shaanxi Institute of Biomedical Materials and Engineering(SIBME)Northwestern Polytechnical University(NPU)Xi'an 710072China College of Innovation and Entrepreneurship Southern University of Science and TechnologyShenzhen 518055China

Ketones are one of the most important classes of organic compounds, and widely present in various pharmacological compounds, biologically active molecules and functional materials. Over the past few decades, transition metal-catalyzed conversion of aldehydes has been found to be a powerful method.With the continuous development in recent years, it has become an efficient and uncomplicated strategy for constructing ketones. There are four major mechanisms for transition metal-catalyzed ketone synthesis from aldehyde:(1) carbonyl-Heck reaction, that is 1,2-insertion of organometal species to aldehydic C=O double bond,(2) direct insertion of transition metal catalysts to aldehydic C-H bond,(3) aldehyde as acyl radical,(4) aldehyde as carbon radical acceptor. This article summarizes related reports on the transformations of aldehydes to generate corresponding ketones under different reaction conditions.

关键词： Homogeneous catalysis transition metal catalysis Direct conversion Ketone synthesis C-H bond functionalization

Recent trends and developments in the asymmetric synthesis of profens

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绿色合成与催化(英文)

绿色合成与催化(英文) 2023年第2期4卷 89-103页

作者： Qiuyue Wang Yuchen Qi Xuefeng Gao Lili Gong Ruiying Wan Weihua Lei Zhenguo Wang Jianyou Mao Haixing Guan Wei Li Patrick J.Walsh College of Pharmacy Shandong University of Traditional Chinese MedicineJinan 250355China Experimental Center Shandong Provincial Key Laboratory of Traditional Chinese Medicine for Basic ResearchShandong University of Traditional Chinese MedicineJinan 250355China Department of Emergency Medicine People's Hospital of Huimin CountyBinzhou 251700China Technical Institute of Fluorochemistry Institute of Advanced SynthesisSchool of Chemistry and Molecular EngineeringNanjing Tech UniversityNanjing 211816China Roy and Diana Vagelos Laboratories Department of ChemistryUniversity of PennsylvaniaPhiladelphia 19104-6323United States

The profens belong to a class of nonsteroidal anti-inflammatory drugs(NSAIDs),which exert significant antiinflammatory,analgesic,antipyretic and other pharmacological effects.A considerable number of catalytic asymmetric strategies for the synthesis of enantioenriched profens have been introduced.Herein are outlined recent trends and developments of promising catalytic enantioselective systems for the generation of profens and their derivatives.According to the reaction type,we divided these transformations into three categories:transition metal-catalyzed asymmetric hydrogenations,transition metal-catalyzed asymmetric cross-couplings and organocatalytic asymmetric transformations.Overviews of generic reaction mechanisms are presented.Ideally,this tutorial review will motivate further interest in the catalytic asymmetric synthesis of highly enantioenriched profens.

关键词： NSAIDs Asymmetric synthesis transition metal catalysis Organocatalysis

Palladium-catalyzed Cycloaromatization Polymerization of Enediynes

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Chinese Journal of Polymer Science 2018年第2期36卷 237-243页

作者： Chonggang Wang Shudan Chen Hao Zhou Jinlou Gu Aiguo Hu Shanghai Key Laboratory of Advanced Polymeric Materials School of Materials Science and Engineering East China University of Science and Technology

Bergman cyclization has shown great promise in constructing conjugated polymers. However, the application of this reaction in polymer science is still limited due to the harsh reaction condition and ill-defined structure of the achieved polymers. To this end, the cycloaromatization polymerization of enediynes catalyzed by a series of transition metal catalysts is investigated in this work, by taking advantage of the coordination chemistry of the enediyne with the transition metal complexes. According to the nuclear magnetic resonance（NMR）, Fourier transform infrared（FTIR）, ultraviolet-visble（UV-Vis） spectroscopies and matrix-assisted laser desorption/ionization time-offlight mass spectrometry（MALDI-TOF MS） analysis, the cycloaromatization polymerization of enediynes proceeds under milder conditions and in a more controlled manner in the presence of palladium（II） complexes, giving structurally regulated conjugated polymers in high yields.

关键词： transition metal catalysis Enediyne Polymerization Cycloaromatization Bergman cyclization

transition metal Catalyzed Enantioselective Borylative Cyclization Reactions

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Chinese Journal of Chemistry 2021年第2期39卷 391-401页

作者： Yuqi Ji Min Zhang Mimi Xing Huanhuan Cui Qian Zhao Chun Zhang Institute of Molecular Plus Tianjin Key Laboratory of Molecular Optoelectronic ScienceDepartment of ChemistrySchool of ScienceTianjin UniversityWeijin Rd.92Tianjin300072 China

Due to the significance of corresponding products,enantioselective borylative cyclization reactions have been studied intensively in recent years.Many groups have developed efficient methods to transform unsaturated system into asymmetric cyclic organoboron compounds with the ring-size range from three-membered to six-membered in general.Notably,in some cases,fused rings which contain more than two contiguous chiral centers could be obtained by this kind of strategies.This review summarized and reviewed the recent advances in this field and classified these work according to the species of metal catalysts.

关键词： Asymmetric synthesis transition metal catalysis Boronation reaction Cyclization reaction Enantioselectivity

Milestones in Molecular Dynamics Simulations of Single-Walled Carbon Nanotube Formation: A Brief Critical Review

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Nano Research 2009年第10期2卷 755-767页

作者： Stephan Irle Yasuhito Ohta Yoshiko Okamoto Alister JPage Ying Wang Keiji Morokuma Fukui Institute for Fundamental Chemistry Kyoto UniversityKyoto 606-8103Japan Institute for Advanced Research and Department of Chemistry Nagoya UniversityNagoya 464-8602Japan Cherry L.Emerson Center for Scientic Computation and Department of Chemistry Emory UniversityAtlantaGA 30322USA Department of Chemistry Nara Women’s UniversityNara 630-8506Japan

We present a brief review of the most important efforts aimed at simulating single-walled carbon nanotube(SWNT)nucleation and growth processes using molecular dynamics(MD)techniques reported in the literature.MD simulations allow the spatio-temporal movement of atoms during nonequilibrium growth to be followed.Thus,it is hoped that a successful MD simulation of the entire SWNT formation process will assist in the design of chirality-specic SWNT synthesis techniques.We give special consideration to the role of the metal catalyst particles assumed in standard theories of SWNT formation,and describe the actual metal behavior observed in the reported MD simulations,including our own recent quantum chemical MD simulations.It is concluded that the use of a quantum potential is essential for a qualitatively correct description of the catalytic behavior of the metal cluster,and that carbide formation does not seem to be a necessary requirement for nucleation and growth of SWNTs according to our most recent quantum chemical MD simulations.

关键词： Carbon nanotubes transition metal catalysis molecular dynamics reactive forceelds quantum chemistry