We thank the National Institutes of Health (GM46059) and the MIT–Singapore Alliance for funding. We are indebted to Merck, Amgen, and Boehringer-Ingelheim for unrestricted support. We are also extremely grateful to Nippon Chemical Co. for providing generous donations of 6–8. We also thank BASF for a donation of palladium acetate.
Palladium-Catalyzed Aminocarbonylation of Aryl Chlorides at Atmospheric Pressure: The Dual Role of Sodium Phenoxide†
Article first published online: 27 SEP 2007
Copyright © 2007 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Angewandte Chemie International Edition
Volume 46, Issue 44, pages 8460–8463, November 12, 2007
How to Cite
Martinelli, Joseph R., Clark, Thomas P., Watson, Donald A., Munday, Rachel H. and Buchwald, Stephen L. (2007), Palladium-Catalyzed Aminocarbonylation of Aryl Chlorides at Atmospheric Pressure: The Dual Role of Sodium Phenoxide. Angew. Chem. Int. Ed., 46: 8460–8463. doi: 10.1002/anie.200702943
- Issue published online: 2 NOV 2007
- Article first published online: 27 SEP 2007
- Manuscript Received: 3 JUL 2007
- National Institutes of Health. Grant Number: GM46059
- MIT–Singapore Alliance
- aryl chlorides;
No pressure, no worries: A general, functional-group-tolerant, mild system for the Pd-catalyzed carbonylation of aryl chlorides to the corresponding amides has been developed. The catalyst operates at 1 atm CO using an inexpensive, air-stable, and commercially available ligand (see scheme, Cy=cyclohexyl). Sodium phenoxide is a critical additive in this transformation; its role has been studied using in situ IR spectroscopy.