Unexpected Reactivity of Nitrones: Catalytic Insertion of CS₂.

ABSTRACT: A new reactivity mode for nitrones is reported, consisting of the chloride-catalyzed insertion of CS₂ to afford thioamides. This reaction proceeds under metal-free and mild conditions, tolerates a broad family of substrates, and is robust and easily scalable, being successfully applied to the synthesis of the HIV-1 reverse transcriptase inhibitor UC-781. Mechanistic studies, supported by DFT calculations, have revealed the role of chloride anions in the activation of CS₂ and its subsequent insertion into nitrones.

SUBMITTER: Lopez-Aguilar M 

PROVIDER: S-EPMC12322958 | biostudies-literature | 2025 Aug

REPOSITORIES: biostudies-literature