This work was supported by ETH Zürich and the Swiss National Science Foundation. We thank Dr. M. Wörle and R. Aardoom for helpful advice concerning X-ray analysis, Dr. J. M. Welch and J. Winkler for experimental assistance, and Dr. E. Zass for an exhaustive literature search concerning NCF3 compounds.
1521-3773/asset/2002_left.gif?v=1&s=ac6b0d94a94d7ce7a210002b8096b42feffc0bcf)
1521-3773/asset/olbannercenter.gif?v=1&s=c083e1920cd41ed129901c116018eab93b5ad3c4)
1521-3773/asset/2002_right.gif?v=1&s=451042aa3415ae3ad0729984d26dee1866aca82e)
Communication
Direct Electrophilic N-Trifluoromethylation of Azoles by a Hypervalent Iodine Reagent†
Article first published online: 22 MAY 2012
DOI: 10.1002/anie.201201572
Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Additional Information
How to Cite
Niedermann, K., Früh, N., Senn, R., Czarniecki, B., Verel, R. and Togni, A. (2012), Direct Electrophilic N-Trifluoromethylation of Azoles by a Hypervalent Iodine Reagent . Angew. Chem. Int. Ed., 51: 6511–6515. doi: 10.1002/anie.201201572
- †
Publication History
- Issue published online: 21 JUN 2012
- Article first published online: 22 MAY 2012
- Manuscript Received: 27 FEB 2012
Funded by
- ETH Zürich
- Swiss National Science Foundation
Keywords:
- electrophilic addition;
- hypervalent compounds;
- nitrogen heterocycles;
- synthetic methods;
- trifluoromethylation
Effective CF3 transfer: Various electron-rich nitrogen heterocycles (pyrazoles, triazoles, and tetrazoles) can be directly N-trifluoromethylated by a hypervalent iodine reagent in an efficient manner. The optimized procedure, which includes an in situ silylation of the substrate followed by an acid-catalyzed CF3 transfer, provides ready access to a series of new and previously challenging or inaccessible NCF3 compounds.