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Umpolung of protons from H2O: a metal-free chemoselective reduction of carbonyl compounds via B2pin2/H2O systems

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Abstract

H2O is routinely described as a proton donor, however, in the presence of diboron compounds, the umpolung reaction of H2O under metal-free conditions was successfully developed, which could afford hydride species, leading to a highly efficient and chemoselective reduction of C[double bond, length as m-dash]O bonds. This strategy exhibits excellent chemoselectivities toward carbonyl groups in the presence of ester, olefin, halogen, thioether, sulfonyl, cyano as well as heteroaromatic groups.

Graphical abstract: Umpolung of protons from H2O: a metal-free chemoselective reduction of carbonyl compounds via B2pin2/H2O systems

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Publication details

The article was received on 02 Apr 2017, accepted on 10 Apr 2017 and first published on 10 Apr 2017


Article type: Paper
DOI: 10.1039/C7OB00820A
Citation: Org. Biomol. Chem., 2017, Advance Article
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    Umpolung of protons from H2O: a metal-free chemoselective reduction of carbonyl compounds via B2pin2/H2O systems

    Q. Xuan, C. Zhao and Q. Song, Org. Biomol. Chem., 2017, Advance Article , DOI: 10.1039/C7OB00820A

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