Catalyst-free chemoselective conjugate addition and reduction of α, β-unsaturated carbonyl compounds via a controllable boration/protodeboronation cascade pathway. Issue 1 (7th December 2017)

• Record Type: Journal Article
• Authors: Huang, Xi; Hu, Junjie; Wu, Mengying; Wang, Jiayi; Peng, Yanqing; Song, Gonghua
• Is Part Of: Green chemistry. Volume 20:Issue 1(2018)
• Page Start: 255
• Page End: 260
• Publication Date: 2017-12-07
• Subjects: Environmental chemistry -- Industrial applications -- Periodicals; Environmental management -- Periodicals; 660
• DOI: 10.1039/c7gc02863f
• Languages: English
• ISSNs: 1463-9262

Abstract

Abstract : A transition-metal-catalyst-free method provides a useful and eco-friendly tool for the chemoselective conjugate addition and reduction of α, β-unsaturated carbonyl compounds. Abstract : 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 Cs2 CO3 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 Cs2 CO3 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.