Selective synthesis of alkylboronates by copper(I)-catalyzed borylation of allyl or vinyl arenes

The Journal of Organic Chemistry
Yanmei WenChaode Li

Abstract

An efficient copper-catalyzed borylation reaction of allyl or vinyl arenes with bis(pinacolato)diboron has been developed, without using ligands. Markovnikov-selectivity is observed in the borylation of allyl arenes with bis(pinacolato)diboron, while the regioselectivity is completely opposite when styrene derivatives are used as substrates. A mechanism involving Cu-B species regioselectively adding olefin double bonds to form the alkylcopper or η(3)-benzyl copper intermediate, which is followed by protonation to obtain products, is proposed.

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Jul 20, 2016·Chemical Reviews·Emily C NeeveTodd B Marder
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Apr 15, 2017·Science·Chao LiPhil S Baran
Dec 12, 2018·Organic Letters·Piyush Kumar VermaK Geetharani
Mar 24, 2020·Organic Letters·Hongliang ZhaoSenmiao Xu

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