Deoxygenation of ClSO2CF2COOMe with Triphenylphosphine for the Metal-Free Direct Electrophilic Difluoroalkylthiolation of Various Heterocycles

A direct electrophilic difluoroalkylthiolation reaction of indole derivatives and other electron-rich heterocycles using methyl 2,2-difluoro-2-(chlorsulfonyl)acetate (ClSO2CF2COOMe) derived from Chen's reagent (FSO2CF2COOMe) is described. The ester group in the product can be further utilized in subsequent versatile transformations. The reactions provide good yields of the corresponding difluoroalkylthiolation products and exhibit high functional group compatibility. It is expected to serve as an alternative and practical protocol for difluoroalkylthiolation of various heterocycles.

Automated summary

A direct electrophilic difluoroalkylthiolation reaction using methyl 2,2-difluoro-2-(chlorsulfonyl)acetate derived from Chen's reagent is described. The reactions provide high yields of the corresponding difluoroalkylthiolation products and exhibit high functional group compatibility, making it a promising alternative protocol for difluoroalkylthiolation of various heterocycles.