Tunable Skeletal Editing of Benzothiazole and Benzisothiazole Via Carbene Transfer Reactions.

ABSTRACT: Understanding how carbene reactivity is modulated by both the heteroarene scaffold and activation mode is critical for advancing selective functionalization strategies. Herein, we report a comparative study revealing the divergent reactivity of benzothiazole and benzisothiazole under both photochemical and metal-catalyzed carbene transfer conditions. Under photochemical conditions, free carbenes induce a stepwise transformation of benzothiazole involving initial carbon-atom exchange followed by carbon atom insertion, affording benzothiazoline and benzothiazine derivatives. In contrast, benzisothiazole undergoes direct monocarbon atom insertion, selectively forming ring-expanded products. Notably, metal-catalyzed carbene transfer does not proceed with aromatic benzothiazole but can efficien

SUBMITTER: Cai BG 

PROVIDER: S-EPMC12648338 | biostudies-literature | 2025 Nov

REPOSITORIES: biostudies-literature