Issue 14, 2022

Nickel/Brønsted acid dual-catalyzed regioselective C–H bond allylation of phenols with 1,3-dienes

Abstract

Selective alkylation of phenols is an efficient strategy for the preparation of phenol derivatives. However, owing to the ambident nucleophilic reactivity of these substrates, chemoselectivity is a predominant challenge in these reactions. Herein, a nickel/Brønsted acid dual-catalyzed regioselective allylation of phenols with 1,3-dienes has been established. In this dual-catalytic pathway, ortho-selective C–H bond allylation of the phenol ring and Markovnikov-selective 1,2-addition of 1,3-dienes were favored. This methodology is characterized by its inexpensive catalyst, broad substrate scope, and good chemo- and regioselectivity.

Graphical abstract: Nickel/Brønsted acid dual-catalyzed regioselective C–H bond allylation of phenols with 1,3-dienes

Supplementary files

Article information

Article type
Research Article
Submitted
20 Apr 2022
Accepted
04 Jun 2022
First published
06 Jun 2022

Org. Chem. Front., 2022,9, 3834-3839

Nickel/Brønsted acid dual-catalyzed regioselective C–H bond allylation of phenols with 1,3-dienes

J. Long, C. Ding and G. Yin, Org. Chem. Front., 2022, 9, 3834 DOI: 10.1039/D2QO00637E

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