Trifluoromethylarene compounds are readily available, and the highly selective cleavage of one C(sp(3))-F bond in trifluoromethyl group is an important strategy to access pharmaceutical molecules containing the gem-difluoro groups. However, there are still some challenges in this field, such as the difficulty in activating the C(sp(3))-F bond and the highly selective cleavage of the single C(sp(3))-F bond. In recent years, efficient methods for the construction of gem-difluoro groups have been developed through the transformation of trifluoromethyl group, in which difluoroalkyl radicals or difluoromethyl carbocation intermediates are alway involved. The recent research progress in this field is summarized based on the cleavage strategies of trifluoromethyl group.