We thank the EPSRC and GSK for funding under the collaborative EPSRC Programme for Synthetic Organic Chemistry with AZ-GSK-Pfizer.
Mild CH Halogenation of Anilides and the Isolation of an Unusual Palladium(I)–Palladium(II) Species†
Article first published online: 12 MAY 2011
Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Angewandte Chemie International Edition
Volume 50, Issue 24, pages 5524–5527, June 6, 2011
How to Cite
Bedford, R. B., Haddow, M. F., Mitchell, C. J. and Webster, R. L. (2011), Mild CH Halogenation of Anilides and the Isolation of an Unusual Palladium(I)–Palladium(II) Species . Angew. Chem. Int. Ed., 50: 5524–5527. doi: 10.1002/anie.201101606
- Issue published online: 1 JUN 2011
- Article first published online: 12 MAY 2011
- Manuscript Revised: 11 APR 2011
- Manuscript Received: 4 MAR 2011
- CH functionalization;
Reducing the load: A facile palladium-catalyzed ortho-selective bromination and chlorination of anilides occurs under aerobic conditions at room temperature when N-halosuccinimides (NXS) are used in the presence of p-toluenesulfonic acid (PTSA). The orthopalladated PTSA complex is not only catalytically competent but also undergoes a reductive process to yield an unusual PdI–PdII tetramer (see structure; Pd green, O red, S yellow, C gray).