Aldol Condensation of Bis(pentafluorophenyl)boron Enolates for the Synthesis of α-Pentafluorophenyl-Substituted α,β-Unsaturated Carbonyl Compounds

α-Pentafluorophenyl-substituted α,β-unsaturated carbonyl compounds are valuable for synthesizing perfluoroarenes. Aldol condensation with pentafluorophenyl-substituted enolates is a highly effective method for their synthesis. This study demonstrates that bis(pentafluorophenyl)boron enolates, featuring a pentafluorophenyl group, readily undergo aldol additions with aldehydes. Subsequent elimination of borinic acid yields α-pentafluorophenyl-substituted α,β-unsaturated carbonyl compounds. Experimental results highlight the crucial role of strong Lewis acidity at the boron center in both aldol addition and borinic acid elimination.