This work was supported in part by a Grant-in-aid for Young Scientists (B) from the MEXT (No. 23750116) and by Project Funding for Basic Science from RIKEN.
Alkene Trifluoromethylation Coupled with CC Bond Formation: Construction of Trifluoromethylated Carbocycles and Heterocycles†
Article first published online: 26 FEB 2013
Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Angewandte Chemie International Edition
Volume 52, Issue 14, pages 4000–4003, April 2, 2013
How to Cite
Egami, H., Shimizu, R., Kawamura, S. and Sodeoka, M. (2013), Alkene Trifluoromethylation Coupled with CC Bond Formation: Construction of Trifluoromethylated Carbocycles and Heterocycles . Angew. Chem. Int. Ed., 52: 4000–4003. doi: 10.1002/anie.201210250
- Issue published online: 26 MAR 2013
- Article first published online: 26 FEB 2013
- Manuscript Received: 23 DEC 2012
- MEXT. Grant Number: 23750116
- homogeneous catalysis
The combo pack: Copper-catalyzed trifluoromethylation of alkenes bearing an allylic proton combined with CC bond formation affords the title compounds in good to high yields (see scheme). The reactions are faster than allylic trifluoromethylation, especially in 1,4-dioxane. A unique 1,6-oxytrifluoromethylation occurred instead of an anticipated seven-membered ring forming carbotrifluoromethylation reaction.