This work was financially supported by The Netherlands Organization for Scientific Research (NWO) by means of a TOP grant to R.V.A.O, and by the Hercules Foundation. We thank Elwin Janssen for technical assistance, Sanne Bouwman for HRMS measurements, and Dr. Andreas W. Ehlers for NMR spectroscopic measurements.
Sustainable Synthesis of Diverse Privileged Heterocycles by Palladium-Catalyzed Aerobic Oxidative Isocyanide Insertion†
Article first published online: 14 NOV 2012
Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Angewandte Chemie International Edition
Volume 51, Issue 52, pages 13058–13061, December 21, 2012
How to Cite
Vlaar, T., Cioc, R. C., Mampuys, P., Maes, B. U. W., Orru, R. V. A. and Ruijter, E. (2012), Sustainable Synthesis of Diverse Privileged Heterocycles by Palladium-Catalyzed Aerobic Oxidative Isocyanide Insertion . Angew. Chem. Int. Ed., 51: 13058–13061. doi: 10.1002/anie.201207410
- Issue published online: 18 DEC 2012
- Article first published online: 14 NOV 2012
- Manuscript Received: 13 SEP 2012
- Netherlands Organization for Scientific Research (NWO)
- Hercules Foundation
- homogeneous catalysis;
O2 in, H2O out: Various diamines and related bisnucleophiles readily undergo oxidative isocyanide insertion with Pd(OAc)2 (1 mol %) as the catalyst and O2 as the terminal oxidant to give a diverse array of medicinally relevant N heterocycles. The utility of this highly sustainable method is demonstrated by a formal synthesis of the antihistamines astemizole and norastemizole.