Nucleophilic sulfur controlled efficient ketothioamide synthesis from tribromomethyl carbinols

Abstract

A greener approach towards diverse α-ketothioamides is demonstrated with a broad substrate scope. The presented protocol establishes the reactivity of the polysulfide derived from elemental sulfur and amines in an aqueous medium.

Regioselective Addition of Sulfur and Amine Nucleophiles To Assemble S═C–S, S–N, and Umpolung C–N Bonds: Exploration of the −CBr3 Group as a Synthetic Equivalent of S═C–S

“…Our recent studies have shown that tribromomethyl carbinol (6) can be efficiently transformed into ketothioamide (7) (Scheme 5a). 20 Under established conditions, the substrates, such as tribromo-methylated adducts derived from activated alkene 21 (8), proceed to the corresponding thioamide formation (Scheme 5b). Further, thioamide (11) was formed from 2-nitro ethylbenzene 22 (10) under established reaction conditions (Scheme 5c).…”