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Aldol Condensation of Bis(pentafluorophenyl)boron Enolates for the Synthesis of α-Pentafluorophenyl-Substituted
Souta Yuruka1, Masatoshi Shibuya2, Yoshihiko Yamamoto1
1Department of Basic Medicinal Sciences, Graduate School of Pharmaceutical Sciences, Nagoya University, Furo-cho, Chikusa, Nagoya 464-8603, Japan.
Abstract:
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.
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