Metal-Free Direct Access to N-Sulfonyl Amidines from Sulfonamides and Secondary Amines Involving Tandem C-N Bond Formations

Nishad, Chandra Shekhar; Haldar, Krishna Kanta; Banerjee, Biplab

Metal-Free Direct Access to N-Sulfonyl Amidines from Sulfonamides and Secondary Amines Involving Tandem C-N Bond Formations

Date

2022-08-17T00:00:00

Authors

Nishad, Chandra Shekhar

Haldar, Krishna Kanta

Banerjee, Biplab

Publisher

American Chemical Society

Abstract

We report a mild and efficient metal-free one-pot procedure for the synthesis of N-sulfonyl amidines via the direct reaction of sulfonamides with secondary amines without using any additives. A wide range of substrates with variety of functional groups is well tolerated under the reaction conditions. Preliminary mechanistic studies indicate that the secondary amine plays a dual role as a C1 source of the amidine group and an aminating agent. Synthetic utility of this method is shown in the late-stage functionalization of drug molecules on the gram scale. � 2022 American Chemical Society.

Keywords

Amides, Amines, Sulfur compounds, amidine, amine, functional group, sulfonamide, Bond formation, Direct reactions, Dual role, Mechanistic studies, Metal free, One-pot procedures, Reaction conditions, Secondary amines, Sulphonamides, Synthetic utility, Article, controlled study, one pot synthesis, synthesis, Additives