Issue 35, 2019

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

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, OCHPh24, NHNCPh25). 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

Supplementary files

Article information

Article type
Communication
Submitted
14 Feb 2019
Accepted
08 Eph 2019
First published
08 Eph 2019

Chem. Commun., 2019,55, 5155-5158

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, 55, 5155 DOI: 10.1039/C9CC01302D

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