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Dual Nickel/Photoredox-Catalyzed Asymmetric Carbosulfonylation of Alkenes.

ABSTRACT: An asymmetric three-component carbosulfonylation of alkenes is presented here. The reaction, involving the simultaneous formation of a C-C and a C-S bond across the π-system, uses a dual nickel/photoredox catalytic system to produce both β-aryl and β-alkenyl sulfones in high yields and with excellent levels of stereocontrol (up to 99:1 er). This protocol exhibits a broad substrate scope and excellent functional group tolerance and its synthetic potential has been demonstrated by successful applications toward pharmacologically relevant molecules. A broad array of control experiments supports the involvement of a secondary alkyl radical intermediate generated through radical addition of a sulfonyl radical to the double bond. Moreover, stoichiometric and cross-over experiments further suggest an underlying Ni(0)/Ni(I)/Ni(III) pathway operative in these transformations.

SUBMITTER: Du X

PROVIDER: S-EPMC10273242 | biostudies-literature | 2023 Jun

REPOSITORIES: biostudies-literature

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Dual Nickel/Photoredox-Catalyzed Asymmetric Carbosulfonylation of Alkenes.

Du Xiaoyong X Cheng-Sánchez Iván I Nevado Cristina C

Journal of the American Chemical Society 20230530 23

An asymmetric three-component carbosulfonylation of alkenes is presented here. The reaction, involving the simultaneous formation of a C-C and a C-S bond across the π-system, uses a dual nickel/photoredox catalytic system to produce both β-aryl and β-alkenyl sulfones in high yields and with excellent levels of stereocontrol (up to 99:1 er). This protocol exhibits a broad substrate scope and excellent functional group tolerance and its synthetic potential has been demonstrated by successful appli ...[more]

PMID: 37249908

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