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Ultrasound in Baylis–Hillman reactions with aliphatic and aromatic aldehydes: scope and limitations

2002; Elsevier BV; Volume: 58; Issue: 37 Linguagem: Inglês

10.1016/s0040-4020(02)00822-0

1464-5416

Fernando Coelho, Wanda P. Almeida, Demetrius Veronese, Cristiano R. Mateus, Elizandra C. Silva Lopes, Rodrigo C. Rossi, Gabriel P. C. Silveira, Cesar Henrique Pavam,

Asymmetric Synthesis and Catalysis

The utilization of ultrasound radiation in the Baylis–Hillman reaction with several aldehydes (aromatics and aliphatics) and different α,β-unsaturated reactants is described. For all aldehydes tested, the utilization of ultrasound sources augmented the reaction rate and the chemical yields. The use of ultrasound with two different catalysts (tri-n-butylphosphine and 1,4-diazabicyclo[2.2.2]octane [DABCO]) was also investigated. It was clearly demonstrated that DABCO is much more effective for catalyzing a Baylis–Hillman reaction under the influence of ultrasound than is tri-n-butylphosphine. No effect on reaction rate was observed when the concentration of DABCO was increased.