Synthesis of Difluoromethanesulfinate Esters by the Difluoromethanesulfinylation of Alcohols

Yuji Sumii; Kenta Sasaki; Okiya Matsubara; Norio Shibata

doi:10.1021/acs.orglett.1c00688

Synthesis of Difluoromethanesulfinate Esters by the Difluoromethanesulfinylation of Alcohols

Org Lett. 2021 Apr 2;23(7):2777-2782. doi: 10.1021/acs.orglett.1c00688. Epub 2021 Mar 19.

Authors

Yuji Sumii¹, Kenta Sasaki¹, Okiya Matsubara¹, Norio Shibata^{1

2

3}

Affiliations

¹ Department of Life Science and Applied Chemistry, Nagoya Institute of Technology, Gokiso, Showa-ku, Nagoya 466-5888, Japan.
² Department of Nanopharmaceutical Sciences, Nagoya Institute of Technology, Gokiso, Showa-ku, Nagoya 466-5888, Japan.
³ Institute of Advanced Fluorine-Containing Materials, Zhejiang Normal University, 688 Yingbin Avenue, 321004 Jinhua, China.

PMID: 33739122
DOI: 10.1021/acs.orglett.1c00688

Abstract

Herein, we report the first synthesis of difluoromethanesulfinate esters via the direct difluoromethanesulfinylation of alcohols with HCF₂SO₂Na/Ph₂P(O)Cl. Primary, secondary, and tertiary alcohols were converted to the corresponding difluoromethanesulfinate esters in good to excellent yields under mild conditions. The late-stage functionalization of complexed biologically active natural products was also demonstrated. The method was extended to the trifluoromethanesulfinylation of alcohols using CF₃SO₂Na in the presence of a catalytic amount of Me₃SiCl to provide trifluoromethanesulfinate esters.

Publication types

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