Catalyst-free chemoselective conjugate addition and reduction of α,β-unsaturated carbonyl compounds via a controllable boration/protodeboronation cascade pathway

• Published in: Green chemistry : an international journal and green chemistry resource : GC 2018, Vol.20 (1), p.255-260
• Main Authors: Huang, Xi, Hu, Junjie, Wu, Mengying, Wang, Jiayi, Peng, Yanqing, Song, Gonghua
• Format: Article
• Language: English
• Subjects: Aldehydes; Carbonyl compounds; Carbonyls; Catalysis; Catalysts; Ethanol; Green chemistry; Metals
• ISSN: 1463-9262; 1463-9270
• DOI: 10.1039/C7GC02863F

A novel, efficient transition-metal-free and controllable boration/protodeboronation strategy has been developed for the chemoselective conjugate addition and 1,4-reduction of α,β-unsaturated carbonyl compounds. Without any metal-catalyst or base, a series of β-boration products of α,β-unsaturated carbonyl compounds was easily obtained in moderate to excellent yields in a mixed solvent of ethanol and water. The presence of a catalytic amount of Cs 2 CO 3 can effectively induce further protodeboronation reaction towards 1,4-reduction products at higher reaction temperature. Therefore, by slightly changing the reaction conditions, the boration or reduction products of α,β-unsaturated carbonyl compounds can be controllably obtained. Mechanistic studies revealed that Cs 2 CO 3 played the key role in activating the protodeboronation step. This transition-metal-catalyst-free and product controllable method provides a useful and eco-friendly tool for the highly chemoselective preparation of the β-boration products and 1,4-reduction products of α,β-unsaturated carbonyl compounds.