These authors contributed equally to this work.
Photo-fluorodecarboxylation of 2-Aryloxy and 2-Aryl Carboxylic Acids†
Article first published online: 28 SEP 2012
Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Angewandte Chemie International Edition
Volume 51, Issue 43, pages 10804–10807, October 22, 2012
How to Cite
Leung, J. C. T., Chatalova-Sazepin, C., West, J. G., Rueda-Becerril, M., Paquin, J.-F. and Sammis, G. M. (2012), Photo-fluorodecarboxylation of 2-Aryloxy and 2-Aryl Carboxylic Acids . Angew. Chem. Int. Ed., 51: 10804–10807. doi: 10.1002/anie.201206352
This work was supported by the University of British Columbia (UBC), the Université Laval, NSERC, the Canadian Research Chair program, a doctoral fellowship from the Consejo Nacional de Ciencia y Tecnología (CONACyT) to M.R.-B., a doctoral fellowship from UBC to C.C.S., and a doctoral fellowship NSERC to J.C.T.L.
- Issue published online: 17 OCT 2012
- Article first published online: 28 SEP 2012
- Manuscript Received: 8 AUG 2012
- University of British Columbia (UBC)
- Université Laval
- Canadian Research Chair program
- radical reactions;
- reaction mechanisms;
- synthetic methods
Coming to light: The title reaction simply requires an aqueous alkaline solution of Selectfluor and light. The method is inexpensive and effective for a wide range of neutral and electron-poor 2-aryloxy and 2-aryl acetic acids to provide fluoromethyl ethers (see scheme) and benzyl fluorides, respectively. The mechanism most likely proceeds through an initial aryl excitation with a subsequent single-electron transfer.