Photoinduced inverse Sonogashira coupling reaction. Issue 25 (9th June 2022)

• Record Type: Journal Article
• Authors: Zhang, Lizhu; Wei, Cunbo; Wu, Jiawen; Liu, Dan; Yao, Yinchao; Chen, Zhuo; Liu, Jianxun; Yao, Chang-Jiang; Li, Dinghua; Yang, Rongjie; Xia, Zhonghua
• Is Part Of: Chemical science. Volume 13:Issue 25(2022)
• Page Start: 7475
• Page End: 7481
• Publication Date: 2022-06-09
• Subjects: Chemistry -- Periodicals; 540.5
• DOI: 10.1039/d2sc01933g
• Languages: English
• ISSNs: 2041-6520

Abstract

Abstract : A transition-metal and photocatalyst-free, photoinduced inverse Sonogashira coupling reaction was developed. Under visible-light irradiation, the excited state iodoalkyne acted as an "alkynyl radical synthetic equivalent". Abstract : Alkynes are widely used in chemistry, medicine and materials science. Here we demonstrate a transition-metal and photocatalyst-free inverse Sonogashira coupling reaction between iodoalkynes and (hetero)arenes or alkenes under visible-light irradiation. Mechanistic and computational studies suggest that iodoalkynes can be directly activated by visible light irradiation, and an excited state iodoalkyne acted as an "alkynyl radical synthetic equivalent", reacting with a series of C(sp 2 )–H bonds for coupling products. This work should open new windows in radical chemistry and alkynylation method.