Difluorocarbene-enabled selective Csp3–N bond cleavage in aliphatic tertiary amines to access sulfilimines and sulfoximines

Abstract

In this study, a metal-free and efficient method for the synthesis of sulfilimines and sulfoximines via difluorocarbene-enabled selective Csp³–N bond cleavage/SN bond formation between tertiary amines and sulfenamides/sulfinamides has been developed. In these reactions, difluoromethylammonium ylides generated in situ using difluorocarbene were necessary for subsequent functionalization. This method featured mild reaction conditions, general substrate scope, and good tolerance of functional groups. In addition, scale-up synthesis, discussion of related applications, and preliminary mechanistic studies were also accomplished.