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Full Paper
Rhodium- and Palladium-Catalyzed Hydroarylation of Propargylic Amines with Arylboronic Acids
Article first published online: 10 FEB 2010
DOI: 10.1002/adsc.200900773
Copyright © 2010 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Additional Information
How to Cite
Arcadi, A., Aschi, M., Chiarini, M., Ferrara, G. and Marinelli, F. (2010), Rhodium- and Palladium-Catalyzed Hydroarylation of Propargylic Amines with Arylboronic Acids. Adv. Synth. Catal., 352: 493–498. doi: 10.1002/adsc.200900773
Publication History
- Issue published online: 17 FEB 2010
- Article first published online: 10 FEB 2010
- Manuscript Received: 6 NOV 2009
Funded by
- Ministero dell′Università e della Ricerca Scientifica e Tecnologica, Rome
- University of L′Aquila
Keywords:
- alkynes;
- arylboronic acids;
- hydroarylation;
- palladium;
- propargylic amines;
- rhodium
Abstract
The hydroarylation of 3-arylprop-2-yn-1-amine derivatives with arylboronic acids has been studied in the presence of rhodium or palladium catalysts. By using a rhodium-based catalytic system, β,γ-diarylallylamines were isolated in good yields. By contrast, the formation of the regiosomeric γ,γ-diarylallylamines was achieved by means of a palladium catalyst in the presence of acetic acid. The complementary regioselectivity displayed by these two processes is a consequence of different catalytic cycles, involving respectively carborhodation or hydropalladation of the coordinated alkyne as key steps. Calculated charge distributions in the π-complexes are in accord with the results obtained.