Issue 25, 2022

Photoinduced inverse Sonogashira coupling reaction

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(sp2)–H bonds for coupling products. This work should open new windows in radical chemistry and alkynylation method.

Graphical abstract: Photoinduced inverse Sonogashira coupling reaction

Supplementary files

Article information

Article type
Edge Article
Submitted
04 Apr. 2022
Accepted
27 Maijs 2022
First published
30 Maijs 2022
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY-NC license

Chem. Sci., 2022,13, 7475-7481

Photoinduced inverse Sonogashira coupling reaction

L. Zhang, C. Wei, J. Wu, D. Liu, Y. Yao, Z. Chen, J. Liu, C. Yao, D. Li, R. Yang and Z. Xia, Chem. Sci., 2022, 13, 7475 DOI: 10.1039/D2SC01933G

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