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Electrochemical radical-polar crossover:a radical approach to polar chemistry

Science China Chemistry 2024年第2期67卷 450-470页

作者： Zhoumei Tan Haonan Zhang Kun Xu Chengchu Zeng Faculty of Environment and Life Beijing University of TechnologyBeijing100124China

radical-polar crossover(RPC) reaction bridges the gap between one-and two-electron reactivities,thus providing an ideal solution to overcome the limitations of both radical and polar chemistry.In this manifold,organic electrochemistry provides a uniquely facile strategy to access a diverse array of radical intermediates,thus broadening the chemical space of the RPC concept.This review highlights the synthetic advances in the field of electrochemical RPC reactions since 2020,with an emphasis on the substrate scope,reaction limitation and mechanistic aspect.The related RPC reactions are categorized as netoxidative,net-reductive,or redox neutral transformations.

关键词： electrosynthesis radical-polar crossover radical chemistry polar chemistry alkene functionalization

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Electrochemical Atom Transfer radical Addition of Polychloroalkanes to Olefins Promoted by 4,4-Di-tert-butyl Bipyridine

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中国化学:英文版 2023年第13期41卷 1583-1588页

作者： Fei Lian Feixian Luo Meng Wang Kun Xu Chengchu Zeng Faculty of Environment and Life Beijing University of TechnologyBeijing100124 China Key Laboratory of Ecology and Environment in Minority Areas(Minzu University of China) National Ethnic Affairs CommissionBeijing100081 China

A new electrochemical strategy for the atom transfer radical addition(ATRA)of polychloroalkanes across olefins has been realized by the synergism of paired electrolysis and halogen bonding activation.Notably,readily accessible 4,4-di-tert-butyl bipyridine(dtbpy),acting as a halogen bonding acceptor,shifted the reduction potential of C—Cl bonds positively by 110 mV.The decreased operating potential leads to a wide substrate scope and excellent functional group compatibility.A diverse array of terminal and internal alkenes such as(hetero)aryl olefins,unactive aliphatic olefins,and natural products and drugs-derived olefins were well compatible.

关键词： Electrocatalysis Organohalides Atom transfer radical addition radical-polar crossover Alkenes

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Expedient Trifluoromethylacylation of Styrenes Enabled by Photoredox Catalysis

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Chinese Journal of Chemistry 2022年第1期40卷 59-64页

作者： Lu Wang Heng Zhang Chuan Zhu Chao Feng Technical Institute of Fluorochemistry(TIF) Institute of Advanced Synthesis(IAS)School of Chemistry and Molecular EngineeringNanjing Tech University30 South Puzhu RoadNanjingJiangsu 211816China

Herein,we disclosed a photoredox enabled protocol for trifluoromethylacylation of styrenes through a radical-carboanion cascade and subsequent oxidation.With a broad range of aldehydes and inexpensive Langlois reagent as acyl and CF3 precursor,respectively,the alkene motif could be readily converted into β-trifluoromethyl ketones in moderate to good yields and with excellent regioselectivity.Besides CF3,di-,mono-and non-fluorinated C-radicals were revealed amenable in this reaction,providing good opportunity for the construction of structurally diverse ketones of interest in pharmaceutical research.Additionally,the utility of this protocol was further demonstrated by successful extension to trifluoromethylarylation and-alkylation by employing arylcyanide or acrylates in place of carbonyls.

关键词： Trifluoromethylacylation Alkenes Photocatalysis CF_(3)radical radical-polar crossover

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