Highly Efficient Synthesis of Multi-Substituted Allenes from Propargyl­ Acetates and Organoaluminum Reagents Mediated by Palladium

Abstract

A simple and mild catalytic S_N2′ substitution reaction of propargyl acetates with organoaluminum reagents is reported. The S_N2′ substitution reaction of propargyl acetates with organoaluminum reagents mediated by Pd(PhP₃)₂Cl₂ (1 mol%)/PPh₃ (2 mol%)/K₂CO₃ in tetrahydrofuran at 60 °C for 3–4 hours afforded the corresponding multi-substituted allenes in good yields (up to 94%) with high selectivities (up to 99%). The process was simple and easily performed, which offers an efficient method to synthesize the multi-substituted allene derivatives.

Key words

allenes - palladium - propargyl acetates - organoaluminum reagent - S_N2′ substitution reaction

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