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Synthesis of Difluoromethanesulfinate Esters by the Difluoromethanesulfinylation of Alcohols

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journal contribution
posted 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.

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