Radical Heck-type reaction of styrenes with sulfonyl hydrazides on water at room temperature. Issue 1 (3rd January 2019)

• Record Type: Journal Article
• Authors: Bao, Wen-Hui; Ying, Wei-Wei; Xu, Xu-Dong; Zhou, Guo-Dong; Meng, Xiao-Xiao; Wei, Wen-Ting; Liu, Yan-Yun; Li, Qiang
• Is Part Of: Tetrahedron letters. Volume 60:Issue 1(2019)
• Page Start: 55
• Page End: 58
• Publication Date: 2019-01-03
• Subjects: Metal-free -- Radical Heck-type reaction -- Room temperature -- Styrenes -- Sulfonyl hydrazides; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2018.11.059
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: Economical TBAI/TBHP system. Water as the sole solvent. Radical Heck-type coupling reaction. Abstract: Herein, metal-free radical Heck-type reaction of styrenes with sulfonyl hydrazides to synthesize vinyl sulfones is developed. The reaction is performed under economical TBAI/TBHP system on water in open air at room temperature, which proceeds through the radical addition to styrenes followed by hydrogen-abstraction. When compared to known approaches for the synthesis of vinyl sulfones from alkenes, this radical Heck-type strategy is practical, green and does not go through HI elimination process. Furthermore, this protocol can be expanded to the iodosulfonylation of alkynes for the synthesis of iodovinyl sulfones.