We thank AstraZeneca PR&D (Dr. M. Kenworthy, Dr. P. M. Murray, Dr. M. Butters) for funding and Thomas Hornsby and Thomas Carter (Bristol Synthesis DTC) for preliminary studies. G.C.L.-J. is a Royal Society Wolfson Research Merit Award Holder.
Preparation of Organotrifluoroborate Salts: Precipitation-Driven Equilibrium under Non-Etching Conditions†
Article first published online: 17 AUG 2012
Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Angewandte Chemie International Edition
Volume 51, Issue 37, pages 9385–9388, September 10, 2012
How to Cite
Lennox, A. J. J. and Lloyd-Jones, G. C. (2012), Preparation of Organotrifluoroborate Salts: Precipitation-Driven Equilibrium under Non-Etching Conditions . Angew. Chem. Int. Ed., 51: 9385–9388. doi: 10.1002/anie.201203930
- Issue published online: 5 SEP 2012
- Article first published online: 17 AUG 2012
- Manuscript Received: 21 MAY 2012
- AstraZeneca PR&D
- synthetic methods;
- tartaric acid;
Simple, rapid, and scaleable: In contrast to current procedures using corrosive HF/MF or MHF2 reagents (M=e.g. K), a wide range of trifluoroborates can be rapidly, simply, and safely prepared from MF (M=K, Cs), RCO2H, and a boronic acid/ester in regular glassware (see figure; left versus right). The use of L-(+)-tartaric acid as an alkali-metal sponge is key and allows isolation of RBF3M by a simple stir/filter/evaporate sequence.