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

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.

SUBMITTER: Liang K

PROVIDER: S-EPMC8150107 | biostudies-literature | 2020 Jan

REPOSITORIES: biostudies-literature

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

Liang Kangjiang K Li Tao T Li Na N Zhang Yang Y Shen Lei L Ma Zhixian Z Xia Chengfeng C

Chemical science 20200110 8

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 ...[more]

PMID: 34123301

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