| Title | Hydrolytic stability of nitrogenous-heteroaryltrifluoroborates under aqueous conditions at near neutral pH |
| Publication Type | Journal Article |
| Year of Publication | 2009 |
| Authors | Li, Y, Asadi, A, Perrin, DM |
| Journal | Journal of Fluorine Chemistry |
| Volume | 130 |
| Pagination | 377-382 |
| Date Published | Apr |
| Type of Article | Article |
| ISBN Number | 0022-1139 |
| Keywords | aryltrifluoroborate, CROSS-COUPLING REACTIONS, F-19 NMR, Heteroaryltrifluoroborates, Hydrolytic stability, PET, PET imaging, POTASSIUM ARYL, SALTS |
| Abstract | The hydrolytic stability of heteroaryltrifluoroborates under physiological conditions has been analyzed by F-19 NMR spectroscopy and is found to be greatly enhanced by the presence of endocyclic ring nitrogens. Stability is further enhanced by the presence of exocyclic electron withdrawing substituents. As with aryltrifluoroborates, NMR analysis suggests that the hydrolysis proceeds via single rate-determining step reflecting loss of the first fluoride atom. The stability of these complexes is significant both in terms of metal catalyzed cross-coupling reactions as well as the potential for generating boronic acid based F-18-PET imaging agents. (C) 2008 Elsevier B.V. All rights reserved. |
| URL | <Go to ISI>://000265313400001 |
