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Hydroboration without a B–H bond: reactions of the borinium cation [(iPr2N)2B]+ with alkyne, nitrile, ketone and diazomethane

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Abstract

The borinium cation [(iPr2N)2B]+ (1+) is shown to react with PhCCH, PhCN, Ph2CO, and Ph2CN2 to effect a net hydroboration, affording borenium complexes of the form [(iPr2N)B(iPrN[double bond, length as m-dash]CMe2)(L)][B(C6F5)4] (L = CH[double bond, length as m-dash]CHPh 2, N[double bond, length as m-dash]CHPh 3, OCHPh2 4, NHNCPh2 5). The nature and reaction of 1+ with PhCCH was probed computationally and the reduction of these unsaturates is shown to occur via hydride transfer from an isopropyl group to the alkyne, thus effecting hydroboration without a B–H bond.

Graphical abstract: Hydroboration without a B–H bond: reactions of the borinium cation [(iPr2N)2B]+ with alkyne, nitrile, ketone and diazomethane

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Publication details

The article was received on 14 Feb 2019, accepted on 08 Apr 2019 and first published on 08 Apr 2019


Article type: Communication
DOI: 10.1039/C9CC01302D
Citation: Chem. Commun., 2019, Advance Article

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    Hydroboration without a B–H bond: reactions of the borinium cation [(iPr2N)2B]+ with alkyne, nitrile, ketone and diazomethane

    C. J. Major, K. L. Bamford, Z. Qu and D. W. Stephan, Chem. Commun., 2019, Advance Article , DOI: 10.1039/C9CC01302D

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