Interception of Secondary Amide Ylide with Sulfonamides: Catalyst-Controlled Synthesis of <i>N</i>‑Sulfonylamidine Derivatives

Abstract

A novel, secondary amide activation strategy has been developed through the in situ generation of ylides from amides and diazoacetates. Under the developed reaction conditions, Mn-catalyzed ylide formation and interception reaction by sulfonamide delivered a variety of N-sulfonylamidines. Notably, when highly active Zn­(OTf)2 was used as the catalyst, further N–H insertion products were obtained. In contrast with traditional methods, our amide activation strategy is distinguished by accessible starting material, inexpensive catalyst, and broad substrate scope