We are deeply appreciative of financial support from the French Ambassy in Germany to A.W. and thank Rhodia Chimie Fine (Dr. F. Metz) for a generous gift of HNTf2.
Gold-Catalyzed Transformation of 2-Alkynyl Arylazides: Efficient Access to the Valuable Pseudoindoxyl and Indolyl Frameworks†
Article first published online: 24 JUN 2011
Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Angewandte Chemie International Edition
Volume 50, Issue 32, pages 7354–7358, August 1, 2011
How to Cite
Wetzel, A. and Gagosz, F. (2011), Gold-Catalyzed Transformation of 2-Alkynyl Arylazides: Efficient Access to the Valuable Pseudoindoxyl and Indolyl Frameworks. Angew. Chem. Int. Ed., 50: 7354–7358. doi: 10.1002/anie.201102707
- Issue published online: 25 JUL 2011
- Article first published online: 24 JUN 2011
- Manuscript Received: 19 APR 2011
- Claisen rearrangement;
- homogeneous catalysis;
- nitrogen heterocycles
An element of surprise: A series of functionalized 2-alkynyl arylazides has beed converted into 3-substituted indoles or 2,2-disubstituted indolin-3-ones in the presence of a gold(I) complex. Various oxygen or aryl nucleophiles can be used in this process to trap the intermediate α-imino gold carbene. The structural motifs of the products are found in a large variety of biologically active compounds and natural products.