Synthesis of gem-Disulfonyl Enamines via an Iminyl-Radical-Mediated Formal 1,3-HAT/Radical Coupling Cascade

Zhongxue Fang; Yujie Zhang; Zhansong Zhang; Qingming Song; Yong Wu; Zhaohong Liu; Yongquan Ning

doi:10.1021/acs.orglett.2c02277

Synthesis of gem-Disulfonyl Enamines via an Iminyl-Radical-Mediated Formal 1,3-HAT/Radical Coupling Cascade

Org Lett. 2022 Sep 9;24(35):6374-6379. doi: 10.1021/acs.orglett.2c02277. Epub 2022 Aug 26.

Authors

Zhongxue Fang¹, Yujie Zhang¹, Zhansong Zhang², Qingming Song², Yong Wu², Zhaohong Liu², Yongquan Ning²

Affiliations

¹ School of Chemistry and Environmental Engineering, Yancheng Teachers University, Yancheng City 224007, People's Republic of China.
² Jilin Province Key Laboratory of Organic Functional Molecular Design & Synthesis, Department of Chemistry, Northeast Normal University, Changchun 130024, People's Republic of China.

PMID: 36018352
DOI: 10.1021/acs.orglett.2c02277

Abstract

We herein report the first example of an iminyl-radical-mediated formal 1,3-HAT/radical coupling cascade of vinyl azides leading to the synthesis of tetrasubstituted gem-disulfonyl enamines. It is possible to employ a variety of vinyl azides and sulfinate salt coupling elements without sacrificing effectiveness and scalability. The combination of experimental studies and DFT calculations showed that this reaction proceeds via a radical addition/formal 1,3-HAT/radical coupling mechanism.