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Issue 6, 2018
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Azaborines: synthesis and use in the generation of stabilized boron-substituted carbocations

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Abstract

A formal N-heterocyclic carbene insertion into the B–H bond of 9-BBN followed by a ring expansion reaction is reported. NHC-9-BBN adducts were reacted in one or two steps to give the corresponding di- or triazaborines. Hydride abstraction of selected species with [Ph3C]+ is facile, giving rise to 6π-aromatic cations with Lewis acidity comparable to Lewis acids commonly employed in frustrated Lewis pairs.

Graphical abstract: Azaborines: synthesis and use in the generation of stabilized boron-substituted carbocations

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Publication details

The article was received on 12 Apr 2017, accepted on 20 Dec 2017 and first published on 20 Dec 2017


Article type: Communication
DOI: 10.1039/C7DT01329A
Citation: Dalton Trans., 2018,47, 1791-1795
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    Azaborines: synthesis and use in the generation of stabilized boron-substituted carbocations

    J. J. Clarke, P. Eisenberger, S. S. Piotrkowski and C. M. Crudden, Dalton Trans., 2018, 47, 1791
    DOI: 10.1039/C7DT01329A

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