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

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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 Cs2CO3 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 Cs2CO3 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.

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

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Publication details

The article was received on 21 Sep 2017, accepted on 24 Nov 2017 and first published on 27 Nov 2017


Article type: Paper
DOI: 10.1039/C7GC02863F
Citation: Green Chem., 2018, Advance Article
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    Catalyst-free chemoselective conjugate addition and reduction of α,β-unsaturated carbonyl compounds via a controllable boration/protodeboronation cascade pathway

    X. Huang, J. Hu, M. Wu, J. Wang, Y. Peng and G. Song, Green Chem., 2018, Advance Article , DOI: 10.1039/C7GC02863F

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