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 abr. 2022
Accepted
27 may. 2022
First published
30 may. 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

This article is licensed under a Creative Commons Attribution-NonCommercial 3.0 Unported Licence. You can use material from this article in other publications, without requesting further permission from the RSC, provided that the correct acknowledgement is given and it is not used for commercial purposes.

To request permission to reproduce material from this article in a commercial publication, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party commercial publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements