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Photoinitiated Three-Component ?-Perfluoroalkyl-?-heteroarylation of Unactivated Alkenes via Electron Catalysis.

ABSTRACT: A visible-light-initiated ?-perfluoroalkyl-?-heteroarylation of various alkenes with perfluoroalkyl iodides and quinoxalin-2(1 H)-ones is presented. This three-component radical cascade reaction allows an efficient synthesis of a range of perfluoroalkyl containing quinoxalin-2(1 H)-one derivatives in moderate to excellent yields under mild conditions. Reactions proceed via acidic aminyl radicals that are readily deprotonated to give the corresponding radical anions able to sustain the radical chain as single electron transfer reducing reagents. Hence, the overall cascade classifies as an electron-catalyzed process.

SUBMITTER: Zheng D

PROVIDER: S-EPMC6326532 | biostudies-literature | 2019 Jan

REPOSITORIES: biostudies-literature

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Photoinitiated Three-Component α-Perfluoroalkyl-β-heteroarylation of Unactivated Alkenes via Electron Catalysis.

Zheng Danqing D Studer Armido A

Organic letters 20181221 1

A visible-light-initiated α-perfluoroalkyl-β-heteroarylation of various alkenes with perfluoroalkyl iodides and quinoxalin-2(1 H)-ones is presented. This three-component radical cascade reaction allows an efficient synthesis of a range of perfluoroalkyl containing quinoxalin-2(1 H)-one derivatives in moderate to excellent yields under mild conditions. Reactions proceed via acidic aminyl radicals that are readily deprotonated to give the corresponding radical anions able to sustain the radical ch ...[more]

PMID: 30576162

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