We thank the EPSRC (GR/R02382 and E061575) and AstraZeneca for support, the joint EPSRC/AstraZeneca/GlaxoSmithKline/Pfizer Organic Studentship Initiative, and Dr. M. Haddow for X-ray crystallography. G.C.L.-J. holds a Royal Society Wolfson Merit Award.
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Communication
Room-Temperature Palladium-Catalyzed C![[BOND]](http://onlinelibrarystatic.wiley.com/undisplayable_characters/00f8ff.gif)
H Activation: ortho-Carbonylation of Aniline Derivatives†
Article first published online: 23 JAN 2009
DOI: 10.1002/anie.200805842
Copyright © 2009 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Issue
Angewandte Chemie International Edition
Volume 48, Issue 10, pages 1830–1833, February 23, 2009
Additional Information
How to Cite
Houlden, Chris E., Hutchby, M., Bailey, Chris D., Ford, J. Gair., Tyler, Simon N. G., Gagné, Michel R., Lloyd-Jones, Guy C. and Booker-Milburn, Kevin I. (2009), Room-Temperature Palladium-Catalyzed CH Activation: ortho-Carbonylation of Aniline Derivatives. Angew. Chem. Int. Ed., 48: 1830–1833. doi: 10.1002/anie.200805842
- †
Publication History
- Issue published online: 17 FEB 2009
- Article first published online: 23 JAN 2009
- Manuscript Received: 1 DEC 2008
Funded by
- EPSRC. Grant Numbers: GR/R02382, E061575
Keywords:
- CH activation;
- carbonylation;
- heterocycles;
- heterogeneous catalysis;
- palladium
Abstract
Pd and CO—ureally got me! The title reaction proceeds efficiently at 18 °C under CO (1 atm) with 5 % [Pd(OTs)2(MeCN)2] as precatalyst. Depending on the solvents used, either anthranilates or cyclic imides can be obtained in high yields (see picture, BQ=benzoquinone, Ts=4-toluenesulfonyl).