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Hydrolytic stability of nitrogenous-heteroaryltrifluoroborates under aqueous conditions at near neutral pH

TitleHydrolytic stability of nitrogenous-heteroaryltrifluoroborates under aqueous conditions at near neutral pH
Publication TypeJournal Article
Year of Publication2009
AuthorsLi, Y, Asadi, A, Perrin, DM
JournalJournal of Fluorine Chemistry
Volume130
Pagination377-382
Date PublishedApr
Type of ArticleArticle
ISBN Number0022-1139
Keywordsaryltrifluoroborate, 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.

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