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Issue 36, 2017
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Reactivity of the geminal phosphinoborane tBu2PCH2BPh2 towards alkynes, nitriles, and nitrilium triflates

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Abstract

The reactivity of the geminal phosphinoborane tBu2PCH2BPh2 towards terminal alkynes, nitriles and nitrilium salts is investigated. Terminal alkynes react via C–H bond splitting (deprotonation) resulting in the formation of phosphonium borates. In contrast, both nitriles and nitrilium salts undergo addition reactions resulting in the formation of five-membered heterocycles. All compounds were characterized by multinuclear NMR spectroscopy, and single-crystal X-ray structure determinations. Insight into the reaction mechanisms was gained by DFT calculations.

Graphical abstract: Reactivity of the geminal phosphinoborane tBu2PCH2BPh2 towards alkynes, nitriles, and nitrilium triflates

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Publication details

The article was received on 14 Jul 2017, accepted on 26 Aug 2017 and first published on 28 Aug 2017


Article type: Paper
DOI: 10.1039/C7DT02570J
Citation: Dalton Trans., 2017,46, 12284-12292
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    Reactivity of the geminal phosphinoborane tBu2PCH2BPh2 towards alkynes, nitriles, and nitrilium triflates

    E. R. M. Habraken, L. C. Mens, M. Nieger, M. Lutz, A. W. Ehlers and J. C. Slootweg, Dalton Trans., 2017, 46, 12284
    DOI: 10.1039/C7DT02570J

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