Abstract An original and efficient copper‐catalyzed 1,6‐hydrodifluoroacetylation of para ‐quinone methides with difluoroalkyl bromides has been described with bis(pinacolato)diboron (B 2 pin 2 ) as reductant. In this reaction, a new C( sp 3 )–CF 2 bond is constructed under smart conditions. A broad substrate scope of para ‐quinone methides ( p ‐QMs) make this protocol very practical and attractive. Preliminary mechanistic studies manifested that a difluoroalkyl radical pathway was involved in this reaction. Also the presence of the diboron reagent was an essential requisite in this transformation. magnified image