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.
1521-3773/asset/2002_left.gif?v=1&s=ac6b0d94a94d7ce7a210002b8096b42feffc0bcf)
1521-3773/asset/olbannercenter.gif?v=1&s=c083e1920cd41ed129901c116018eab93b5ad3c4)
1521-3773/asset/2002_right.gif?v=1&s=451042aa3415ae3ad0729984d26dee1866aca82e)
Communication
Preparation of Organotrifluoroborate Salts: Precipitation-Driven Equilibrium under Non-Etching Conditions†
Article first published online: 17 AUG 2012
DOI: 10.1002/anie.201203930
Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Issue
Angewandte Chemie International Edition
Volume 51, Issue 37, pages 9385–9388, September 10, 2012
Additional Information
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
- †
Publication History
- Issue published online: 5 SEP 2012
- Article first published online: 17 AUG 2012
- Manuscript Received: 21 MAY 2012
Funded by
- AstraZeneca PR&D
Keywords:
- boron;
- fluorine;
- synthetic methods;
- tartaric acid;
- trifluoroborates
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.