Mn-Mediated Electrochemical Trifluoromethylation/C(sp2)-H Functionalization Cascade for the Synthesis of Azaheterocycles

Zhenxing Zhang; Lei Zhang; Yang Cao; Feng Li; Guangcan Bai; Guoquan Liu; Yang Yang; Fanyang Mo

doi:10.1021/acs.orglett.8b04010

Mn-Mediated Electrochemical Trifluoromethylation/C(sp²)-H Functionalization Cascade for the Synthesis of Azaheterocycles

Org Lett. 2019 Feb 1;21(3):762-766. doi: 10.1021/acs.orglett.8b04010. Epub 2019 Jan 23.

Authors

Zhenxing Zhang, Lei Zhang, Yang Cao, Feng Li, Guangcan Bai, Guoquan Liu, Yang Yang¹, Fanyang Mo

Affiliation

¹ Division of Chemistry and Chemical Engineering , California Institute of Technology , Pasadena , California 91125 , United States.

PMID: 30672710
DOI: 10.1021/acs.orglett.8b04010

Abstract

A general electrohemical strategy for the combined trifluoromethylation/C(sp²)-H functionalization using Langlois' reagent as the CF₃ source under oxidant-free conditions was developed. Using Mn salts as the redox mediator, this method provides an efficient and sustainable means to access a variety of functionalized heterocycles bearing a CF₃ moiety. Detailed mechanistic studies are consistent with the formation of CF₃-bound high oxidation state Mn species, suggesting a transition-metal-mediated CF₃ transfer mechanism for this trifluoromethylation/C(sp²)-H functionalization process.

Publication types

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