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Redox-neutral photochemical Heck-type arylation of vinylphenols activated by visible light

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Abstract

Disclosed herein is a photochemical Heck-type arylation of vinylphenols with non-activated aryl and heteroaryl halides under visible light irradiation. Preliminary mechanistic studies suggested that the colored vinylphenolate anions acted as a strong reducing photoactivator to directly activate (hetero)aryl halides without the need for any sacrificial reductants. The photochemically generated aryl radicals coupled with another molecule of vinylphenol to afford the Heck-type arylation product in a regiospecific and stereoselective manner. The developed photochemical arylation protocol showed exceptional functional group tolerance and was successfully applied in the challenging late-stage modification of natural products without any protection–deprotection procedures.

Graphical abstract: Redox-neutral photochemical Heck-type arylation of vinylphenols activated by visible light

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Article information


Submitted
06 Dec 2019
Accepted
10 Jan 2020
First published
10 Jan 2020

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2020, Advance Article
Article type
Edge Article

Redox-neutral photochemical Heck-type arylation of vinylphenols activated by visible light

K. Liang, T. Li, N. Li, Y. Zhang, L. Shen, Z. Ma and C. Xia, Chem. Sci., 2020, Advance Article , DOI: 10.1039/C9SC06184C

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