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Issue 91, 2018
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Mechanistic and asymmetric investigations of the Au-catalysed cross-coupling between aryldiazonium salts and arylboronic acids using (P,N) gold complexes

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Abstract

In order to explore the different mechanisms possibly occurring in the Au-catalysed cross-coupling of ArN2BF4 and ArB(OH)2 in the presence of CsF, various stoichiometric experiments were performed on gold complexes with (P,N) ligands. Employing 2-pyridylphenyl-diphenylphosphine allowed us to suggest three different mechanistic pathways, starting either with a transmetallation step, via two consecutive single electron transfers, or by implying a transmetallation between Au(I) and Au(III) species. Moreover, when using commercially available chiral (P,N) ligands, the asymmetric formation of atropoisomeric biaryls from suitable aryldiazonium salts and arylboronic acids could be achieved with e.e. up to 26%.

Graphical abstract: Mechanistic and asymmetric investigations of the Au-catalysed cross-coupling between aryldiazonium salts and arylboronic acids using (P,N) gold complexes

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Publication details

The article was received on 17 Sep 2018, accepted on 19 Oct 2018 and first published on 30 Oct 2018


Article type: Communication
DOI: 10.1039/C8CC07530A
Citation: Chem. Commun., 2018,54, 12867-12870
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    Mechanistic and asymmetric investigations of the Au-catalysed cross-coupling between aryldiazonium salts and arylboronic acids using (P,N) gold complexes

    A. Tabey, M. Berlande, P. Hermange and E. Fouquet, Chem. Commun., 2018, 54, 12867
    DOI: 10.1039/C8CC07530A

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