Silver-Promoted Site-Selective Intramolecular Cyclization of 2-Methylthiobenzamide Through α-C(sp3)-H Functionalization

Ke Yang; Ben Niu; Zhiyan Ma; Hui Wang; Brianna Lawrence; Haibo Ge

doi:10.1021/acs.joc.9b02202

Silver-Promoted Site-Selective Intramolecular Cyclization of 2-Methylthiobenzamide Through α-C(sp³)-H Functionalization

J Org Chem. 2019 Nov 1;84(21):14045-14052. doi: 10.1021/acs.joc.9b02202. Epub 2019 Oct 17.

Authors

Ke Yang¹, Ben Niu², Zhiyan Ma¹, Hui Wang¹, Brianna Lawrence², Haibo Ge²

Affiliations

¹ Jiangsu Key Laboratory of Advanced Catalytic Materials & Technology, School of Petrochemical Engineering , Changzhou University , 1 Gehu Road , Changzhou , Jiangsu 213164 , China.
² Department of Chemistry and Chemical Biology , Indiana University Purdue University Indianapolis , Indianapolis , Indiana 46202 , United States.

PMID: 31589040
DOI: 10.1021/acs.joc.9b02202

Abstract

Silver-mediated intramolecular α-C(sp³)-H bond functionalization of the methylthio group has been established in the presence of Selectfluor as an additive. This novel strategy provides efficient access to various diverse sulfur-based heterocycles with good yields and functional group compatibility. It is noteworthy that the completely novel benzooxathiin-4-imine skeletons were reported for the first time in this study.

Publication types

Research Support, Non-U.S. Gov't
Research Support, U.S. Gov't, Non-P.H.S.