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Electrochemical Borylation of Alkyl Halides: Fast, Scalable Access to Alkyl Boronic Esters.

Bingbing WangPan PengWan MaZhao LiuCheng HuangYangmin CaoPing HuXiaotian QiQingquan Lu
Published in: Journal of the American Chemical Society (2021)
Herein, a fast, scalable, and transition-metal-free borylation of alkyl halides (X = I, Br, Cl) enabled by electroreduction is reported. This process provides an efficient and practical access to primary, secondary, and tertiary boronic esters at a high current. More than 70 examples, including the late-stage borylation of natural products and drug derivatives, are furnished at room temperature, thereby demonstrating the broad utility and functional-group tolerance of this protocol. Mechanistic studies disclosed that B2cat2 serves as both a reagent and a cathodic mediator, enabling electroreduction of difficult-to-reduce alkyl bromides or chlorides at a low potential.
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