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On the Redox Properties of the Dimers of Thiazol-2-ylidenes That Are Relevant for Radical Catalysis.


ABSTRACT: We report the isolation and study of dimers stemming from popular thiazol-2-ylidene organocatalysts. The model featuring 2,6-di(isopropyl)phenyl (Dipp) N-substituents was found to be a stronger reducing agent (Eox = -0.8 V vs SCE) than bis(thiazol-2-ylidenes) previously studied in the literature. In addition, a remarkable potential gap between the first and second oxidation of the dimer also allows for the isolation of the corresponding air-persistent radical cation. The latter is an unexpected efficient promoter of the radical transformation of α-bromoamides into oxindoles.

SUBMITTER: Delfau L 

PROVIDER: S-EPMC10251502 | biostudies-literature | 2023 Jun

REPOSITORIES: biostudies-literature

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