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Decarboxylative Borylation of Stabilized and Activated Carbon Radicals.

Qiang ZhangXiaojuan LiWeigang ZhangShengyang NiYi WangYi Pan
Published in: Angewandte Chemie (International ed. in English) (2020)
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-CF3 substituted substrates could be activated for further elaboration.
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