We are deeply appreciative of financial support from Ecole Polytechnique to A.P. and G.H. and from ANR to P.F., and we thank Rhodia Chimie Fine (Dr. F. Metz) for a generous gift of HNTf2.
Gold-Catalyzed Synthesis of Functionalized Pyridines by Using 2H-Azirines as Synthetic Equivalents of Alkenyl Nitrenes†
Article first published online: 8 APR 2014
© 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Angewandte Chemie International Edition
Volume 53, Issue 19, pages 4959–4963, May 5, 2014
How to Cite
Prechter, A., Henrion, G., Faudot dit Bel, P. and Gagosz, F. (2014), Gold-Catalyzed Synthesis of Functionalized Pyridines by Using 2H-Azirines as Synthetic Equivalents of Alkenyl Nitrenes. Angew. Chem. Int. Ed., 53: 4959–4963. doi: 10.1002/anie.201402470
- Issue published online: 2 MAY 2014
- Article first published online: 8 APR 2014
- Manuscript Received: 15 FEB 2014
- Ecole Polytechnique
- homogeneous catalysis;
2H-Azirines are easily synthesized from the corresponding ketones and, despite possessing a CN bond embedded in a strained three-membered cycle, they are sufficiently stable to be isolated, stored, and manipulated. 2H-Azirines can be regarded as valuable synthetic equivalents of alkenyl nitrenes, however, reactions capitalizing on the cyclic strain of the heterocyclic motif and involving the cleavage of the CN single bond remain surprisingly limited. A gold-catalyzed reaction that allows the formation of polysubstituted functionalized pyridines from easily accessible 2-propargyl 2H-azirine derivatives was developed. This transformation, which corresponds to an unprecedented intramolecular transfer of an alkenyl nitrene to an alkyne, proceeds with low catalyst loading, is efficient, and exhibits a high functional-group tolerance and a wide substrate scope.