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Para-Selective C-H Borylation of Common Arene Building Blocks Enabled by Ion-Pairing with a Bulky Countercation

Madalina T. Mihai, Benjamin D. Williams and Robert J. Phipps*

*Department of Chemistry, University of Cambridge, Lensfield Road, Cambridge CB2 1EW, United Kingdom, Email: rjp71cam.ac.uk

M. T. Mihai, B. D. Williams, R. J. Phipps, J. Am. Chem. Soc., 2019, 141, 15477-15482.

DOI: 10.1021/jacs.9b07267 (free Supporting Information)


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Abstract

A remarkably general, iridium-catalyzed  borylation results in para-selectivity on some of the most common arene building blocks (anilines, benzylamines, phenols, benzyl alcohols) using standard borylation ligands. The strategy relies on a facile conversion of the substrates into sulfate or sulfamate salts, wherein the anionic arene component is paired with a tetrabutylammonium cation.

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Key Words

borylation


ID: J48-Y2019