Halodifluoromethyl and trifluoromethyl-containing compounds are widely employed in organic chemistry, pharmaceuticals and materials science. Therefore, their applications and transformations have received significant attention during the past few decades. The single, double, triple and quadruple cleavage of halodifluoromethyl compounds and various deconstructive modes of trifluoromethyl-containing compounds could generate a variety of synthons to prepare more valuable products. Herein, we summarize the most significant achievements in this field with an intriguing focus on results from the last decade.