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Atom Transfer Radical Polymerization of Functionalized Vinyl Monomers Using Perylene as a Visible Light Photocatalyst
Published on: April 22, 2016
Redox-neutral photochemical Heck-type arylation of vinylphenols activated by visible light
Kangjiang Liang1, Tao Li1, Na Li1
1Key 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 xiacf@ynu.edu.cn.
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.
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