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Full Paper
Rapid Room Temperature Buchwald–Hartwig and Suzuki–Miyaura Couplings of Heteroaromatic Compounds Employing Low Catalyst Loadings
Article first published online: 21 APR 2006
DOI: 10.1002/chem.200600283
Copyright © 2006 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Additional Information
How to Cite
Navarro, O., Marion, N., Mei, J. and Nolan, S. P. (2006), Rapid Room Temperature Buchwald–Hartwig and Suzuki–Miyaura Couplings of Heteroaromatic Compounds Employing Low Catalyst Loadings. Chemistry - A European Journal, 12: 5142–5148. doi: 10.1002/chem.200600283
Publication History
- Issue published online: 16 JUN 2006
- Article first published online: 21 APR 2006
- Manuscript Received: 1 MAR 2006
Keywords:
- Buchwald–Hartwig reaction;
- carbenes;
- cross-coupling;
- palladium;
- Suzuki–Miyaura reaction
Graphical Abstract
A matter of minutes: The use of second-generation [(NHC)Pd(R-allyl)Cl] complexes permits the Buchwald–Hartwig and the Suzuki–Miyaura coupling reactions of N-containing heteroaromatic halides to occur extremely rapidly and/or at very low catalyst loadings even at room temperature.
Abstract
The use of second-generation [(NHC)Pd(R-allyl)Cl] complexes for Suzuki–Miyaura and Buchwald–Hartwig cross-coupling reactions involving heteroaromatic halides at room temperature is reported. The first examples of room temperature Suzuki–Miyaura cross-coupling of deactivated aryl chlorides with alkenyl boronic acids are also disclosed. Terminal substitution at the allyl moiety of the palladium complex facilitates its activation at room temperature leading to very active catalytic species enabling the present catalytic transformations to be performed rapidly using very mild reaction conditions. Catalyst loadings can be as low as 10 ppm for the Buchwald–Hartwig aryl amination and 50 ppm for the Suzuki–Miyaura reaction.