Interception of Secondary Amide Ylide with Sulfonamides: Catalyst-Controlled Synthesis ofN-Sulfonylamidine Derivatives

Jijun Chen,Wenhao Long,Yonggang Yang^*（杨永刚）, andXiaobing Wan^*（万小兵）

Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science,Soochow University,Suzhou215123,P. R. China

Org. Lett.,2018,20(9), 2663--2666

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 ofN-sulfonylamidines. Notably, when highly active Zn(OTf)₂was 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.

链接：https://pubs.acs.org/doi/10.1021/acs.orglett.8b00867