Rh-catalyzed C–N coupling of N-sulfonyl-1,2,3-trizales with secondary amines for regioselective synthesis of phenylvinyl-1,2-diamines

Abstract

An efficient and operationally simple method for the preparation of phenylvinyl-1,2-diamines by the Rh(II)-catalyzed C–N coupling of 1-sulfonyl-1H-1,2,3-triazoles with secondary amines (e.g., N-aryl glycine esters, diarylamines or 1-phenyl-2-(p-tolylamino)ethanone) via the 1,3-insertion of Rh(II)-azavinyl carbenes into sp³ N-H bond process has been developed. The optimized conditions tolerate various functional groups and afford the diverse (Z)-phenylvinyl-1,2-diamines in good to excellent yields with high regioselectivity. The method was also successfully extended to the synthesis of functional tertiary amines having a Z configuration of the (1-aryl-2-(sulfonamido)vinyl) substituent and two aryl groups.

Graphical Abstract

Keywords:

• Carbenes
• glycine esters
• n-sulfonyl-1,2,3-trizales
• phenylvinyl-1,2-diamines
• secondary amines

Additional information

Funding

The work was partially supported by the National Natural Science Foundation of China (No. 21772001), the Anhui Provincial Natural Science Foundation [No. 1808085MB41].