Just Published in Organic Letters

Authors: Lujia Mao, Kálmán J. Szabó*, Todd B. Marder*

Abstract: Alcohols are among the most abundant and readily available organic feedstocks in industrial processes. The direct catalytic functionalization of sp3 C–O bonds of alcohols remains the main challenge in this field. Here, we report a copper-catalyzed synthesis of benzyl-, allyl-, and allenyl-boronates from benzylic, allylic, and propargylic alcohols, respectively. This protocol exhibits a broad reaction scope (40 examples) and high efficiency (up to 95% yield) under mild conditions, including for the preparation of secondary allylic boronates. Preliminarily mechanistic studies suggest that nucleophilic substitution is involved in this reaction.

Link: http://pubs.acs.org/doi/abs/10.1021/acs.orglett.7b00256