Redox-neutral photochemical Heck-type arylation of vinylphenols activated by visible light
By: Kangjiang Liang, Tao Li, Na Li, Yang Zhang, Lei Shen, Zhixian Ma and Chengfeng Xia*
Key Laboratory of Medicinal Chemistry for Natural Resource (Ministry of Education and Yunnan Province), State Key Laboratory for Conservation and Utilization of Bio-Resources in Yunnan, School of Chemical Science and Technology, Library of Yunnan University, Yunnan University, 2 North Cuihu Road, Kunming 650091, China
Chemical Science 2020, 11, 2130
DOI: 10.1039/c9sc06184c
Publication Date (Web): January 10, 2020
Document Type: Article
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.
https://pubs.rsc.org/en/content/articlelanding/2020/SC/C9SC06184C#!divAbstract
