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Issue 48, 2012
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Essential role of phosphines in organocatalytic β-boration reaction

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Abstract

The use of phosphines to assist the organocatalytic β-boration reaction of α,β-unsaturated carbonyl compounds has been demonstrated with a selected number of substrates. The new method eludes the use of Brönsted bases to promote the catalytic active species and PR3 becomes essential to interact with the substrate resulting in the formation of a zwitterionic phosphonium enolate. This species can further deprotonate MeOH when B2pin2 is present forming eventually the ion pair [α-(H),β-(PR3)-ketone]+[B2pin2·MeO] that is responsible for the catalysis.

Graphical abstract: Essential role of phosphines in organocatalytic β-boration reaction

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Publication details

The article was received on 27 Sep 2012, accepted on 24 Oct 2012 and first published on 25 Oct 2012


Article type: Paper
DOI: 10.1039/C2OB26899J
Citation: Org. Biomol. Chem., 2012,10, 9677-9682
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    Essential role of phosphines in organocatalytic β-boration reaction

    C. Pubill-Ulldemolins, A. Bonet, H. Gulyás, C. Bo and E. Fernández, Org. Biomol. Chem., 2012, 10, 9677
    DOI: 10.1039/C2OB26899J

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