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Issue 31, 2016
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Bench-stable frustrated Lewis pair chemistry: fluoroborate salts as precatalysts for the C–H borylation of heteroarenes

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Abstract

While the organotrifluoroborate group is commonly used as a leaving group in cross-coupling reactions, we now show that their high stability can be used to protect the Lewis acidic moieties of frustrated Lewis pair catalysts. Indeed, the air and moisture-stable trifluoro- and difluoroborate derivatives of bulky (tetramethylpiperidino)benzene are shown to be conveniently converted to their dihydroborane analogue which is known to activate small molecules. An efficient synthesis route to these stable and convenient precatalysts, their deprotection chemistry and their benchtop use for the dehydrogenative borylation of heteroarenes is presented.

Graphical abstract: Bench-stable frustrated Lewis pair chemistry: fluoroborate salts as precatalysts for the C–H borylation of heteroarenes

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Publication details

The article was received on 10 Feb 2016, accepted on 12 Mar 2016 and first published on 14 Mar 2016


Article type: Communication
DOI: 10.1039/C6CC01267A
Citation: Chem. Commun., 2016,52, 5387-5390
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    Bench-stable frustrated Lewis pair chemistry: fluoroborate salts as precatalysts for the C–H borylation of heteroarenes

    M. Légaré, É. Rochette, J. Légaré Lavergne, N. Bouchard and F. Fontaine, Chem. Commun., 2016, 52, 5387
    DOI: 10.1039/C6CC01267A

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