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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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Article information


Submitted
12 Apr 2017
Accepted
20 Dec 2017
First published
20 Dec 2017

Dalton Trans., 2018,47, 1791-1795
Article type
Communication

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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