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Organophotocatalytic carbo-heterofunctionalization of unactivated olefins with pendant nucleophiles.

ABSTRACT: We report the difunctionalization of unactivated, terminal olefins through intermolecular addition of α-bromoketones, -esters, and -nitriles followed by formation of 4- to 6-membered heterocycles with pendant nucleophiles. The reaction can be conducted with alcohols, acids, and sulfonamides as nucleophiles furnishing products bearing 1,4 functional group relationships that offer various handles for further manipulation. Salient features of the transformations are the use of 0.5 mol% of a benzothiazinoquinoxaline organophotoredox catalyst and their robustness with respect to air and moisture. Mechanistic investigations are carried out and a catalytic cycle for the reaction is proposed.

SUBMITTER: Fischer DM

PROVIDER: S-EPMC10321488 | biostudies-literature | 2023 Jul

REPOSITORIES: biostudies-literature

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Organophotocatalytic carbo-heterofunctionalization of unactivated olefins with pendant nucleophiles.

Fischer David M DM Freis Manuel M Amberg Willi M WM Lindner Henry H Carreira Erick M EM

Chemical science 20230614 26

We report the difunctionalization of unactivated, terminal olefins through intermolecular addition of α-bromoketones, -esters, and -nitriles followed by formation of 4- to 6-membered heterocycles with pendant nucleophiles. The reaction can be conducted with alcohols, acids, and sulfonamides as nucleophiles furnishing products bearing 1,4 functional group relationships that offer various handles for further manipulation. Salient features of the transformations are the use of 0.5 mol% of a benzoth ...[more]

PMID: 37416720

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