The authors thank the EPSRC (to Z.G., M.T., M.H.), the CRUK (to Z.G., M.T.), GSK (to M.H.), the A*STAR NSS Overseas Ph.D. Scholarship (to Y.H.L.), the K. C. Wong Education Foundation (to L.L.), and Advion BioSystems for generous funding, Dr. John M. Brown FRS for discussions and Dr. Oscar Lozano for technical assistance.
Metal-Free Oxidative Fluorination of Phenols with [18F]Fluoride†
Article first published online: 25 MAY 2012
Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Angewandte Chemie International Edition
Volume 51, Issue 27, pages 6733–6737, July 2, 2012
How to Cite
Gao, Z., Lim, Y. H., Tredwell, M., Li, L., Verhoog, S., Hopkinson, M., Kaluza, W., Collier, T. L., Passchier, J., Huiban, M. and Gouverneur, V. (2012), Metal-Free Oxidative Fluorination of Phenols with [18F]Fluoride. Angew. Chem. Int. Ed., 51: 6733–6737. doi: 10.1002/anie.201201502
- Issue published online: 27 JUN 2012
- Article first published online: 25 MAY 2012
- Manuscript Revised: 5 APR 2012
- Manuscript Received: 23 FEB 2012
- K. C. Wong Education Foundation
- fluoride ions;
- phenol umpolung;
The radiochemical synthesis of [18F]4-fluorophenols is based on phenol umpolung under oxidative conditions and direct nucleophilic fluorination with [18F]fluoride (see scheme, TBAF=tetra-n-butylammonium fluoride, TFA=trifluoroacetic acid). Readily available O-unprotected 4-tert-butyl phenols are used as precursors in this one-pot protocol. The reaction is completed in less than 30 minutes at room temperature and can be performed using standard or microfluidic technology.