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.
Yuruka et al. (Thu,) studied this question.