Cai Tao, Shen Fangqi, Ni Yuqi, Xu Huiting, Shen Runpu, Gao Yuzhen
College of Chemistry and Chemical Engineering, Shaoxing University, Shaoxing 312000, China.
College of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou 730070, China.
J Org Chem. 2021 Jan 1;86(1):1002-1011. doi: 10.1021/acs.joc.0c02444. Epub 2020 Dec 7.
An efficient method for the direct preparation of 3-aceto(cyano)methyl-substituted benzothio(seleno)phenes has been achieved through C(sp)-H bond activation of easily available acetone or acetonitrile and cascade radical cyclization reaction. In this cascade radical cyclization reaction, C(sp)-C(sp) and C(sp)-S bonds, as well as benzenethio(seleno)phene skeletons, can be built along with the cleavage of the C(sp)-S bond, demonstrating the high step-economics and efficiency of this approach.
