One-pot synthesis of α,α-difluoroimines from alkynes through tandem catalytic diboration/fluorination/imination reaction

Tandem catalytic diboration/fluorination/imination of arylacetylenes leads to the formation of α,α-difluoroimines, where the adjacent CN and C–F2 bonds are formed simultaneously. The convenient one-pot protocol involves a Pt(0)-catalyzed diboration of terminal or internal arylalkynes followed by electrophilic fluorination with Selectfluor in the presence of primary amines and a dehydrating agent. A plausible mechanism for the three consecutive steps (diboration/fluorination/imination) is suggested in accordance with the electronic properties of the substrates. Alkynes/catalytic diboration/alkenyl diboronate esters/Selectfluor/electrophilic fluorination/α,α-difluoroimines.