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Recent advances in transition-metal catalyzed nitrene transfer reactions with carbamates

Chinese Chemical Letters 2024年第3期35卷 76-86页

作者： Yanshu Luo Xinyu Zhang Yuanzhi Xia College of Chemistry and Materials Engineering Wenzhou UniversityWenzhou 325035China

Nitrene transfer reactions are powerful tools in synthetic organic chemistry.In recent years,transitionmetal catalyzed nitrene transfer reactions with carbamates as the nitrene precursors have been widely pursued.Such species undergoes facile C-H amination,aziridination,and bifunctionalization of alkenes under the catalysis of different transition metals including Rh,Fe,Ru and others,enabling the efficient construction of various nitrogen-containing molecules.In this review,the recent developments in nitrene transfer reactions with carbamates via N-O bond cleavage were introduced based on different types of reaction,and the key mechanistic information and synthetic applications of the methodologies were discussed.

关键词： transition-metal catalysis Nitrene transfer Carbamate C—H amination Aziridination Bifunctionalization

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Natural products inspired[3+2]cycloaddition enables efficient construction of hydroxylated tetrahydrofuran acetals and concise syntheses of lignans

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Science China Chemistry 2024年第7期67卷 2306-2313页

作者： Dong-Yue Cai Weiming Shi Zhao-Hui Jin Zhi-Xiang Yu Jin-Xin Zhao Jian-Min Yue State Key Laboratory of Drug Research Shanghai Institute of Materia MedicaChinese Academy of SciencesShanghai 201203China University of Chinese Academy of Sciences Beijing 100049China Beijing National Laboratory for Molecular Sciences(BNLMS) Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of EducationCollege of ChemistryPeking UniversityBeijing 100871China

Mimicking biosynthetic pathways of hongkonoids led to the development of a new Cu(Ⅰ)-catalyzed[3+2]cycloaddition ofα-hydroxyketone andβ-keto enol ethers,affording tetrahydrofuran acetals in a highly diastereoselective manner and 100%atom economy.Computational studies on the mechanism disclosed a concerted but asynchronous Michael addition/aldol reaction.Of the same importance,this methodology provides a practical biomimetic approach for one-step construction of the dibenzylbutyrolactol lignan backbone starting from two phenyl propane derivatives,opening up a powerful new approach for lignan synthesis,which is showcased by succinct total syntheses of two biologically important aryltetralin-type lignans,β-apopicropodophyllin and cycloolivil.Given the mild and operationally simple conditions,the developed chemistry might have a promising prospect in potential industrial applications.

关键词： [3+2]cycloaddition transition-metal catalysis tetrahydrofuran lignans natural products

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Synthesis of[60]Fullerene-Fused Allylbenzofurans via Palladium-Catalyzed Migration Reaction

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中国化学:英文版 2023年第14期41卷 1733-1739页

作者： Tong-Xin Liu Panting Yang Nana Ma Xiaojun Li Xin Wang Jinliang Ma Guisheng Zhang Collaborative Innovation Center of Henan Province for Green Manufacturing of Fine Chemicals Key Laboratory of Green Chemical Media and ReactionsMinistry of EducationSchool of Chemistry and Chemical EngineeringHenan Normal UniversityXinxiangHenan453007 China

Chemical functionalization of fullerenes has been an important topic in fullerene chemistry. Herein, an unprecedented Pd-catalyzed migration reaction of [60]fullerene with allyloxy-tethered aryl iodides is present for the preparation of novel [60]fullerene-fused allylbenzofurans. The use of 1,2-bis(diphenylphosphino)benzene (DPPBz) as a ligand is crucial for the success of the transformation. The reaction shows high chemo- and regioselectivity, and is flexible with regard to allyl-migration site, providing a new and efficient approach to rare [60]fullerene-fused benzofurans. Control experiments disclose that the reaction most probably undergoes a sequential C—O bond cleavage/allyl-migration/intermolecular cycloaddition cascade process.

关键词： Fullerenes transition-metal catalysis Cross-coupling Cycloaddition Oxygen heterocycles

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Recent advances in the construction of axially chiral arylpyrroles

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中国科学:化学英文版 2023年第9期66卷 2480-2491页

作者： Yang-Bo Chen Ye-Nan Yang Xuan-Zhu Huo Long-Wu Ye Bo Zhou Key Laboratory of Chemical Biology of Fujian Province State Key Laboratory of Physical Chemistry of Solid SurfacesCollege of Chemistry and Chemical EngineeringXiamen UniversityXiamen 361005China State Key Laboratory of Organometallic Chemistry Shanghai Institute of Organic ChemistryChinese Academy of SciencesShanghai 200032China

Catalytic enantioselective preparation of axially chiral molecules has gained considerable interest over the past decades, due to their numerous applications in bioactive molecules, natural products, pharmaceuticals, materials, ligands, and catalysts. Compared with the well-established synthetic approaches for six-membered axially chiral skeletons, methodologies directed towards five-membered axially chiral compounds are relatively rare. Among these, axially chiral arylpyrroles are especially important structural motifs with wide utility, and the atroposelective synthesis of them is highly desirable. In recent years, novel strategies have been developed based on transition-metal catalysis and organocatalysis. This review summarizes the recent achievements in atroposelective preparation of arylpyrroles, by emphasizing the synthetic methods for each axially chiral framework, reaction mechanisms, and applications.

关键词： axial chirality pyrrole atropisomers transition-metal catalysis organocatalysis

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Recent Applications of Homogeneous catalysis in Electrochemical Organic Synthesis

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CCS Chemistry 2022年第4期4卷 1120-1152页

作者： Xu Cheng Aiwen Lei Tian-Sheng Mei Hai-Chao Xu Kun Xu Chengchu Zeng School of Chemistry and Chemical Engineering Nanjing UniversityNanjing 210023 College of Chemistry and Molecular Sciences Institute for Advanced Studies(IAS)Wuhan UniversityWuhan 430072 State Key Laboratory of Organometallic Chemistry Center for Excellence in Molecular SynthesisShanghai Institute of Organic ChemistryUniversity of Chinese Academy of SciencesChinese Academy of SciencesShanghai 200032 State Key Laboratory of Physical Chemistry of Solid Surfaces College of Chemistry and Chemical EngineeringXiamen UniversityXiamen 361005 Faculty of Environment and Life Beijing University of TechnologyBeijing 100124

Although the combination of electrochemistry and homogeneous catalysis has proven to be a powerful strategy for achieving a diverse array of novel transformations,some challenges such as controlling the diffusion of catalyst-related species and the instability of catalysts at electrodes remain to be overcome.Herein,we review recent advances in electrochemical homogeneous catalysis,focusing on electrochemical noble-transition-metal catalysis,photoelectrochemical catalysis,and electrochemical enantioselective catalysis.The topics discussed include:(1)how the noblemetal catalystworks in the presence of cathodic hydrogen evolution,(2)how the photocatalyst gets enhanced redox property,and(3)how the enantioselectivity is regulated in a catalytic electrochemical reaction.

关键词： electrochemistry homogeneous catalysis transition-metal catalysis electrophotocatalysis enantioselective catalysis

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Progress and challenges in dicarboxylation with CO_(2)

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National Science Open 2023年第2期2卷 1-36页

作者： Chuan-Kun Ran Han-Zhi Xiao Li-Li Liao Tao Ju Wei Zhang Da-Gang Yu Key Laboratory of Green Chemistry&Technology of Ministry of Education College of ChemistrySichuan UniversityChengdu 610064China School of Chemistry and Chemical Engineering Chongqing UniversityChongqing 400030China College of Chemistry and Chemical Engineering Yangzhou UniversityYangzhou 225002China

Dicarboxylic acids,which are appealing structural motifs in organic synthesis and exist widely in bioactive compounds,have been widely used as important monomers in the polymer industry to construct valuable materials.The dicarboxylation with CO_(2)provides a convenient and potent way to furnish value-added dicarboxylic acids via the chemical fixation of two CO_(2)molecules.Beyond any doubt,the development of dicarboxylation,especially the dicarboxylation of bulk chemicals,might represent a promising prospect in CO_(2)capture and utilization(CCU).In this review,we critically summarized and comprehensively reviewed the advances made in the past decades in dicarboxylation with CO_(2)under electro-,photo-and transition metal-mediated/catalytic systems.Moreover,the advantages and limitations of such dicarboxylation reactions are pointed out to unravel further development for future scientific and industrial advances in dicarboxylation with CO_(2)to synthesize dicarboxylic acids in high selectivity and efficiency.

关键词： carbon dioxide dicarboxylation electrochemistry photoredox catalysis transition-metal catalysis

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