This work was partly supported by Grants-in-Aid from the Ministry of Education, Culture, Sports, Science, and Technology (Japan). K.H. acknowledges the Kansai Research Foundation for the Promotion of Science.
Nickel- and Cobalt-Catalyzed Direct Alkylation of Azoles with N-Tosylhydrazones Bearing Unactivated Alkyl Groups†
Article first published online: 7 DEC 2011
Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Angewandte Chemie International Edition
Volume 51, Issue 3, pages 775–779, January 16, 2012
How to Cite
Yao, T., Hirano, K., Satoh, T. and Miura, M. (2012), Nickel- and Cobalt-Catalyzed Direct Alkylation of Azoles with N-Tosylhydrazones Bearing Unactivated Alkyl Groups. Angew. Chem. Int. Ed., 51: 775–779. doi: 10.1002/anie.201106825
- Issue published online: 12 JAN 2012
- Article first published online: 7 DEC 2011
- Manuscript Revised: 18 NOV 2011
- Manuscript Received: 26 SEP 2011
- Ministry of Education, Culture, Sports, Science, and Technology (Japan)
- Kansai Research Foundation for the Promotion of Science
- CH functionalization;
A matter of catalyst: Azole compounds can be directly alkylated with N-tosylhydrazones that bear unactivated alkyl groups (see scheme; phen=1,10-phenanthroline, Ts=p-toluenesulfonyl). Nickel catalysis enables the introduction of simple secondary alkyl chains into benzoxazole compounds, whereas the alkylation of 5-aryloxazoles and benzothiazole is possible by using a cobalt catalyst.