Synthesis of Difluoromethanesulfinate Esters by the Difluoromethanesulfinylation of Alcohols
journal contributionposted on 19.03.2021, 16:08 by Yuji Sumii, Kenta Sasaki, Okiya Matsubara, Norio Shibata
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.