Synthesis of <i>gem</i>-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
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.
Topics & Concepts
ChemistryCascadeRadical cyclizationCoupling (piping)RadicalCombinatorial chemistryComputational chemistryStereochemistryOrganic chemistryMechanical engineeringChromatographyEngineeringSulfur-Based Synthesis TechniquesRadical Photochemical ReactionsCatalytic C–H Functionalization Methods