Novel Sc(OTf)₃/3-HQD Catalyst for Morita–Baylis–Hillman Reaction

Abstract

A novel and efficient catalytic system of the Morita–Baylis–Hillman (MBH) reaction between aromatic aldehyde and activated alkenes has been developed. The novel system of a combination of Sc(OTf)₃ and 3-hydroxyquinuclidine (3-HQD) showed a high catalytic activity for the MBH reaction.

Keywords:

• 3-Hydroxyquinuclidine
• Morita–Baylis–Hillman reaction
• Sc(OTf)₃

Notes

^a Reaction conditions: 3.0 mmol of methyl acrylate, 1.0 mmol of p-nitrobenzaldehyde, 100 mmol% of Lewis base using CH₃CN as solvent.

^b Isolated yield based on p-nitrobenzaldehyde.

^a Isolated yield based on p-nitrobenzaldehyde.

^a Reaction conditions: 3.0 mmol of α,β-unsaturated ester, 1.0 mmol of aromatic aldehydes, 5 mmol% of Sc(OTf)₃, and 20 mmol% of Lewis base using DMF as solvent.

^b Isolated yield based on aromatic aldehyde.