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Issue 87, 2016
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B(C6F5)3-Catalyzed transfer 1,4-hydrostannylation of α,β-unsaturated carbonyls using iPr-tricarbastannatrane

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Abstract

Tris(pentafluorophenyl)borane, B(C6F5)3, has been found to be an effective catalyst to access the hydridoborate anion, [N(CH2CH2CH2)3Sn][HB(C6F5)3], via hydride abstraction from the hypercoordinated tin reagent, iPr-tricarbastannatrane. This process has been applied to the B(C6F5)3-catalyzed transfer 1,4-hydrostannylation of electron-deficient olefins, namely benzylidene barbituric acids. Insights into the mechanism have been obtained via a series of 1H, 2H, 11B, 13C, and 119Sn NMR spectroscopy, mass spectrometry, and labeling experiments.

Graphical abstract: B(C6F5)3-Catalyzed transfer 1,4-hydrostannylation of α,β-unsaturated carbonyls using iPr-tricarbastannatrane

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Publication details

The article was received on 26 Sep 2016, accepted on 06 Oct 2016 and first published on 07 Oct 2016


Article type: Communication
DOI: 10.1039/C6CC07819B
Citation: Chem. Commun., 2016,52, 12813-12816
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    B(C6F5)3-Catalyzed transfer 1,4-hydrostannylation of α,β-unsaturated carbonyls using iPr-tricarbastannatrane

    E. Fillion, A. Kavoosi, K. Nguyen and C. Ieritano, Chem. Commun., 2016, 52, 12813
    DOI: 10.1039/C6CC07819B

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