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Late-Stage Heteroarylation of Hetero(aryl)sulfonium Salts Activated by α-Amino Alkyl Radicals.

ABSTRACT: We report a late-stage heteroarylation of aryl sulfonium salts through activation with α-amino alkyl radicals in a mechanistically distinct approach from previously reported halogen-atom transfer (XAT). The new mode of activation of aryl sulfonium salts proceeds in the absence of light and photoredox catalysts, engaging a wide range of hetarenes. Furthermore, we demonstrate the applicability of this methodology in synthetically useful cross-coupling transformations.

SUBMITTER: Alvarez EM

PROVIDER: S-EPMC8251951 | biostudies-literature | 2021 Jun

REPOSITORIES: biostudies-literature

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Late-Stage Heteroarylation of Hetero(aryl)sulfonium Salts Activated by α-Amino Alkyl Radicals.

Alvarez Eva Maria EM Karl Teresa T Berger Florian F Torkowski Luca L Ritter Tobias T

Angewandte Chemie (International ed. in English) 20210505 24

We report a late-stage heteroarylation of aryl sulfonium salts through activation with α-amino alkyl radicals in a mechanistically distinct approach from previously reported halogen-atom transfer (XAT). The new mode of activation of aryl sulfonium salts proceeds in the absence of light and photoredox catalysts, engaging a wide range of hetarenes. Furthermore, we demonstrate the applicability of this methodology in synthetically useful cross-coupling transformations. ...[more]

PMID: 33835680

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