This work was supported the European Community (MRTN-CT-2003-505020, MEIF-CT-2006-039270 and MEIF-CT-2006-040558) and the EPSRC (GR/S79268/02). We thank G. Giuffredi and A. Monney for performing selected experiments, and A. L. Thompson of the Oxford Chemical Crystallography Service for X-ray studies.
Gold(I)-Catalyzed Alkoxyhalogenation of β-Hydroxy-α,α-Difluoroynones†
Article first published online: 6 AUG 2008
Copyright © 2008 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Angewandte Chemie International Edition
Volume 47, Issue 41, pages 7927–7930, September 29, 2008
How to Cite
Schuler, M., Silva, F., Bobbio, C., Tessier, A. and Gouverneur, V. (2008), Gold(I)-Catalyzed Alkoxyhalogenation of β-Hydroxy-α,α-Difluoroynones. Angew. Chem. Int. Ed., 47: 7927–7930. doi: 10.1002/anie.200802162
- Issue published online: 24 SEP 2008
- Article first published online: 6 AUG 2008
- Manuscript Received: 8 MAY 2008
- European Community. Grant Numbers: MRTN-CT-2003-505020, MEIF-CT-2006-039270, MEIF-CT-2006-040558
- EPSRC. Grant Number: GR/S79268/02
- homogeneous catalysis;
Gold standard: AuCl was found to be the only suitable catalyst for the 6-endo-dig ring closure of hydroxylated difluorinated ynones (see scheme), a class of substrates that displays low reactivity owing to the presence of the gem-difluoro group. For the first time, a gold catalyst is used in combination with an electrophilic fluorinating reagent.