A Catalytic Aldol Reaction and Condensation through In Situ Boron “Ate” Complex Enolate Generation in Water

Aelvoet, K.; Batsanov, A. S.; Blatch, A. J.; Grosjean, C.; Patrick, L. G. F.; Smethurst, C. A.; Whiting, A.

Abstract

Cooperation is key: N-Butyl-1-benzimidazole-2-phenylboronic acid hydroxide complex catalyzes the aldol condensation and aldol addition between hydroxyacetone or acetone, and different aldehydes in water. The catalytic activity results from cooperative interactions between the boronate complex and the imidazole function. Aldol condensation gives the unsaturated methyl ketones of acetone, whereas aldol addition predominates with hydroxyacetone.

Citation

Aelvoet, K., Batsanov, A. S., Blatch, A. J., Grosjean, C., Patrick, L. G. F., Smethurst, C. A., & Whiting, A. (2008). A Catalytic Aldol Reaction and Condensation through In Situ Boron “Ate” Complex Enolate Generation in Water. Angewandte Chemie International Edition, 47(4), 768-770. https://doi.org/10.1002/anie.200704293

• Journal Article Type: Article
• Publication Date: 2008-01
• Journal: Angewandte Chemie International Edition
• Print ISSN: 1433-7851
• Electronic ISSN: 1521-3773
• Publisher: Wiley
• Peer Reviewed: Peer Reviewed
• Volume: 47
• Issue: 4
• Pages: 768-770
• DOI: https://doi.org/10.1002/anie.200704293
• Keywords: aldol reaction; bifunctional catalysts; boron; homogeneous catalysis; selectivity
• Public URL: https://durham-repository.worktribe.com/output/1566305