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Reduction of unactivated alkyl chlorides enabled by light-induced single electron transfer

Science China Chemistry 2024年第2期67卷 471-481页

作者： Lei Dai Zhao-Fei Zhang Xiang-Yu Chen School of Chemical Sciences University of the Chinese Academy of SciencesBeijing100049China Institute of Chemistry Chinese Academy of SciencesBeijing100190China Binzhou Institute of Technology Weiqiao-UCAS Science and Technology ParkBinzhou256606China

alkyl chlorides are abundant and easily accessible starting materials.However,due to the high reduction potentials associated with unactivated alkyl chlorides,achieving their single electron reduction remains a persistent challenge.This challenge has spurred the exploration of efficient activation methods to overcome this issue.In recent years,photocatalysis has emerged as a mild and potent tool for the single electron reduction of unactivated alkyl chlorides,opening up new possibilities in this field.Considering the rapid advancements in this area,a comprehensive review that provides a conceptual understanding of this emerging field,with a specific focus on reaction design and catalytic mechanisms,would be timely and highly valuable.Hence,we present an overview of various synthetic techniques for photoinduced single electron reduction of unactivated alkyl chlorides.Furthermore,we also discuss the limitations of the present methods and future directions that lie ahead in this field.

关键词： photocatalysis unactivated alkyl chlorides single electron transfer radical reactions

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Iron-Catalyzed Borylation and Silylation of unactivated Tertiary,Secondary,and Primary alkyl chlorides

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CCS Chemistry 2021年第9期3卷 2164-2173页

作者： Siyu Wang Minghui Sun Huan Zhang Juan Zhang Yun He Zhang Feng Chongqing Key Laboratory of Natural Product Synthesis and Drug Research School of Pharmaceutical SciencesChongqing UniversityChongqing 401331 Sichuan Key Laboratory of Medical Imaging Department of ChemistrySchool of Preclinical MedicineNorth Sichuan Medical CollegeSichuan 637000

Herein,we describe an iron-catalyzed borylation and silylation of unactivated alkyl chlorides,delivering the tertiary,secondary,and primary alkylboronic esters,and secondary,primary alkylsilanes with high efficiency.This protocol exhibits broad substrate scope and good functional group compatibility,allowing the efficient late-stage borylation of biorelevant compounds,thus offering an excellent platform in drug discovery and development.Preliminary mechanistic studies suggest that an alkyl radical was involved in this catalytic system.

关键词： iron catalysis borylation silylation unactivated alkyl chlorides

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