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Institute for sustainable chemistry & catalysis with boron - ICB

Just Published in Organic Letters

02/24/2017

Synthesis of Benzyl-, Allyl-, and Allenyl-boronates via Copper-Catalyzed Borylation of Alcohols

 

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

By Dr. Rian Dewhurst

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