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Decarboxylative Borylation of Stabilized and Activated Carbon Radicals
Author(s) -
Zhang Qiang,
Li Xiaojuan,
Zhang Weigang,
Ni Shengyang,
Wang Yi,
Pan Yi
Publication year - 2020
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.202008138
Subject(s) - borylation , radical , chemistry , carbon fibers , photochemistry , materials science , organic chemistry , composite material , composite number , alkyl , aryl
Redox‐active esters (RAEs) as active radical precursors have been extensively studied for C−B bond formations. However, the analogous transformations of stabilized radicals from the corresponding acid precursors remain challenging owing to the strong preference towards single‐electron oxidation to the stable carbocations. This work describes a general strategy for rapid access to various aliphatic and aromatic boronic esters by mild photoinduced decarboxylative borylation. Both aryl and alkyl radicals could be generated from the leaving group‐assisted N‐hydroxybenzimidoyl chloride esters, even α‐CF 3 substituted substrates could be activated for further elaboration.