Synthesis of amides via TBN-induced oxidation cross-coupling of acetonitrile and N-sulfinylanilines

A novel method for the synthesis of amides has been developed that features – tert-butyl nitrite-induced oxidative cross-coupling of acetonitrile with N-sulfinylanilines. Acetonitrile serves as the C2 building block in this process. The present protocol effectively inhibits the competition with the C≡N triple bond but enables the in situ formation of unsaturated C–O bond. The reaction demonstrates a broad substrate scope and can be conducted under mild conditions. Mechanistic studies, including radical trapping experiments and H₂¹⁸O-labeling, confirm a radical-mediated pathway involving acetonitrile-derived intermediates. Additionally, this method is amenable to gram-scale synthesis.