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Issue 1, 2016
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Chemoselective catalytic reduction of conjugated α,β-unsaturated ketones to saturated ketones via a hydroboration/protodeboronation strategy

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Abstract

A novel copper-catalyzed chemoselective reduction of a carbon–carbon double or triple bond to a carbon–carbon single bond in α,β-unsaturated ketones is developed. This reaction proceeds under hydrogen gas or stoichiometric metal hydride free conditions. Saturated ketones were obtained in good to excellent yields with a broad substrate scope. Mechanistic studies reveal that the two hydrogen atoms come from H2O in the system. Thus this reaction represents a highly efficient, and remarkably chemoselective strategy.

Graphical abstract: Chemoselective catalytic reduction of conjugated α,β-unsaturated ketones to saturated ketones via a hydroboration/protodeboronation strategy

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Publication details

The article was received on 17 Sep 2015, accepted on 21 Oct 2015 and first published on 26 Oct 2015


Article type: Research Article
DOI: 10.1039/C5QO00289C
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Org. Chem. Front., 2016,3, 14-18

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    Chemoselective catalytic reduction of conjugated α,β-unsaturated ketones to saturated ketones via a hydroboration/protodeboronation strategy

    W. Ding and Q. Song, Org. Chem. Front., 2016, 3, 14
    DOI: 10.1039/C5QO00289C

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