Visible-light-driven graphitic carbon nitride-catalyzed ATRA of alkynes: highly regio- and stereoselective synthesis of (E)-β-functionalized vinylsulfones

Shu-Li Xie, Jian-Zhong Yan, Meng-Jun Xie, Xuan Li, Fan Zhou,

Mei-Qiong Zheng, Xue-Lin Wang, Junhao Feng, Yao Zhang, Ya-Nan Duan, Yong-Dong Niu,* Dong Li* and Hai-Dong Xia*

Green Chem. 2024, 26, 323-329.

Recently, the Hai-Dong Xia team from the School of Chemistry and Chemical Engineering (School of Carbon Neutrality Future Technology) at Shantou University made new progress in the research field of " Organic photochemical synthesis." The related research findings were published under the title "Visible-light-driven graphitic carbon nitride-catalyzed ATRA of alkynes: highly regio- and stereoselective synthesis of (E)-β-functionalized vinylsulfones" in the top journal "Green Chem." (impact factor 10.6) in the field of organic chemistry.

Paper link:

https://doi. org/10.1039/d3gc02897f

English abstract of the paper:

Heterogeneous photocatalysis has emerged as a powerful and sustainable technique in organic synthesis; however, the application of graphitic carbon nitride (g-C3N4) as a heterogeneous photocatalyst for organic transformations is still in its infancy. The development of novel organic transformations catalyzed by g-C3N4 is actively being pursued by chemists but it remains challenging. Herein, we describe a visiblelight-driven g-C3N4-catalyzed atom transfer radical addition (ATRA) of alkynes to synthesize valuable (E)- β-thio/seleno vinylsulfones. This approach features heterogeneous photocatalysis, excellent regio- and stereoselectivities, 100% atom economy, a metal- and additive-free nature, and broad substrate scope covering (hetero)aryl and alkyl alkynes, especially the industrial feedstock propyne. Furthermore, this method can be applied to the late-stage functionalization of complex molecules. Notably, g-C3N4 can be recovered and reused in five runs without loss of catalytic activity. Mechanistic studies demonstrate that the reaction occurs via an energy transfer process rather than single electron transfer.