A Metal-Free Diverse Synthesis of Difluoromethylthioethers and Difluorobis(arylthio)methanes from RSX (X = SR, Cl, SO2Ph) and TMSCF2H

Jia-Bin Han; Hua-Li Qin; Su-Hong Ye; Lei Zhu; Cheng-Pan Zhang

doi:10.1021/acs.joc.6b00089

A Metal-Free Diverse Synthesis of Difluoromethylthioethers and Difluorobis(arylthio)methanes from RSX (X = SR, Cl, SO2Ph) and TMSCF2H

J Org Chem. 2016 Mar 18;81(6):2506-12. doi: 10.1021/acs.joc.6b00089. Epub 2016 Mar 9.

Authors

Jia-Bin Han¹, Hua-Li Qin¹, Su-Hong Ye¹, Lei Zhu², Cheng-Pan Zhang¹

Affiliations

¹ School of Chemistry, Chemical Engineering and Life Science, Wuhan University of Technology , 205 Luoshi Road, Wuhan, 430070, China.
² College of Chemistry and Materials Science, Hubei Engineering University , Hubei, 432000, China.

PMID: 26932358
DOI: 10.1021/acs.joc.6b00089

Abstract

Construction of difluoromethylthioethers (2) and difluorobis(arylthio)methanes (3) from RSX (X = SR, Cl, SO2Ph) and TMSCF2H in the absence of transition metals has been explored. The reaction is dramatically influenced by the nature of the base and the molar ratio of the reactants. Reactions between RSX and TMSCF2H in the presence of CsF provided 2 in good yields, whereas the reaction of RSX with TMSCF2H in the presence of t-BuOK afforded 3 in good yields. These protocols allow for convenient and efficient access to both difluoromethylthioethers and difluorobis(arylthio)methanes.

Publication types

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