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Issue 65, 2016
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Gold-catalysed cross-coupling between aryldiazonium salts and arylboronic acids: probing the usefulness of photoredox conditions

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Abstract

The synthesis of biaryl compounds from aryldiazonium salts and arylboronic acids was achieved using PPh3AuCl as catalyst, CsF as base and acetonitrile as solvent. Combined to photosensitizers, irradiation by blue LEDs allowed accelerating the reaction and expanding its scope. Various functional groups were compatible including bromoaryls, iodoaryls, aldehydes and alcohols. A 2-iodobenzyl alcohol moiety was smoothly introduced by this method, enabling its consecutive isotopic labelling by a Pd-catalysed alkoxycarbonylation.

Graphical abstract: Gold-catalysed cross-coupling between aryldiazonium salts and arylboronic acids: probing the usefulness of photoredox conditions

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Supplementary files

Article information


Submitted
19 May 2016
Accepted
19 Jul 2016
First published
25 Jul 2016

Chem. Commun., 2016,52, 10040-10043
Article type
Communication

Gold-catalysed cross-coupling between aryldiazonium salts and arylboronic acids: probing the usefulness of photoredox conditions

T. Cornilleau, P. Hermange and E. Fouquet, Chem. Commun., 2016, 52, 10040 DOI: 10.1039/C6CC04239B

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