Cascade Radical Annulation of 2-Alkynylthio(seleno)anisoles with Acetone or Acetonitrile: Synthesis of 3-Acetomethyl- or Cyanomethyl-Substituted Benzothio(seleno)phenes

Tao Cai; Fangqi Shen; Yuqi Ni; Huiting Xu; Runpu Shen; Yuzhen Gao

doi:10.1021/acs.joc.0c02444

Cascade Radical Annulation of 2-Alkynylthio(seleno)anisoles with Acetone or Acetonitrile: Synthesis of 3-Acetomethyl- or Cyanomethyl-Substituted Benzothio(seleno)phenes

J Org Chem. 2021 Jan 1;86(1):1002-1011. doi: 10.1021/acs.joc.0c02444. Epub 2020 Dec 7.

Authors

Tao Cai¹, Fangqi Shen², Yuqi Ni¹, Huiting Xu¹, Runpu Shen¹, Yuzhen Gao³

Affiliations

¹ College of Chemistry and Chemical Engineering, Shaoxing University, Shaoxing 312000, China.
² College of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou 730070, China.
³ Key Laboratory of Coal to Ethylene Glycol and Its Related Technology, Fujian Institute of Research on the Structure of Matter, Chinese Academy of Sciences, Fuzhou, Fujian 350002, China.

PMID: 33284023
DOI: 10.1021/acs.joc.0c02444

Abstract

An efficient method for the direct preparation of 3-aceto(cyano)methyl-substituted benzothio(seleno)phenes has been achieved through C(sp³)-H bond activation of easily available acetone or acetonitrile and cascade radical cyclization reaction. In this cascade radical cyclization reaction, C(sp²)-C(sp³) and C(sp²)-S bonds, as well as benzenethio(seleno)phene skeletons, can be built along with the cleavage of the C(sp³)-S bond, demonstrating the high step-economics and efficiency of this approach.