@article {POC:POC3403,
	title = {Designing kinetically stable aryltrifluoroborates as 18F-capture agents for PET imaging},
	journal = {Journal of Physical Organic Chemistry},
	volume = {28},
	number = {3},
	year = {2015},
	pages = {210{\textendash}214},
	abstract = {One-step 18F-radiolabeling of peptides and other large biomolecules has been challenged by a critical gap in chemical compatibility between fluoride anion, which is unreactive as a nucleophile in water, and large biomolecules such as peptides that are insoluble in dry solvents. Traditionally, this disparity has been overcome through the preliminary synthesis of an 18F-labeled radioprosthetic group that is appended to peptides following at least one additional step. Ideally, however, peptides should be labeled in a single aqueous step. Hence, we proposed the use of arylboronic acids as captors of aqueous 18F-fluoride ion to simplify the radiosynthesis of 18F-aryltrifluoroborate bioconjugates. Yet, the use of aryltrifluoroborates as radioprosthetic groups can only be considered if kinetically stable ones can be designed. Herein, we discuss the kinetic and thermodynamic parameters review our previous use of a Hammett analysis that can inform the design of kinetically stable~18F-labeled aryltrifluoroborates for use as novel radioprosthetic groups. Copyright {\textcopyright} 2014 John Wiley \& Sons, Ltd.},
	keywords = {aryltrifluoroborate, FLUORIDE, hammett, PET imaging, solvolysis},
	issn = {1099-1395},
	doi = {10.1002/poc.3403},
	url = {http://dx.doi.org/10.1002/poc.3403},
	author = {Liu, Zhibo and Li, Ying and Ting, Richard and Perrin, David M.}
}
@article {2501,
	title = {Hydrolytic stability of nitrogenous-heteroaryltrifluoroborates under aqueous conditions at near neutral pH},
	journal = {Journal of Fluorine Chemistry},
	volume = {130},
	number = {4},
	year = {2009},
	note = {ISI Document Delivery No.: 434ZRTimes Cited: 4Cited Reference Count: 16Li, Ying Asadi, Ali Perrin, David M.},
	month = {Apr},
	pages = {377-382},
	type = {Article},
	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.},
	keywords = {aryltrifluoroborate, CROSS-COUPLING REACTIONS, F-19 NMR, Heteroaryltrifluoroborates, Hydrolytic stability, PET, PET imaging, POTASSIUM ARYL, SALTS},
	isbn = {0022-1139},
	url = {<Go to ISI>://000265313400001},
	author = {Li, Y. and Asadi, A. and Perrin,David M.}
}
@article {2289,
	title = {Capturing aqueous [F-18]-fluoride with an arylboronic ester for PET: Synthesis and aqueous stability of a fluorescent [F-18]-labeled aryltrifluoroborate},
	journal = {Journal of Fluorine Chemistry},
	volume = {129},
	number = {5},
	year = {2008},
	note = {ISI Document Delivery No.: 302SWTimes Cited: 5Cited Reference Count: 12Ting, Richard Lo, Justin Adam, Michael J. Ruth, Thomas J. Perrin, David M.},
	month = {May},
	pages = {349-358},
	type = {Article},
	abstract = {The aqueous stability of aryltrifluoroborates is of importance to their use in transition metal mediated coupling reactions as well as their potential use in [F-18]-labeled aryltrifluoroborate PET imaging agents. Nevertheless, few studies have fully characterized the solvolysis of fluoride from an aryltrifluoroborate in water. Using [F-19] NMR, fluorescence and [F-18]-labeling techniques, we disclose the composition of an aryltrifluoroborate of exceptional kinetic stability with respect to solvolytic defluoridation. This work not only highlights the potential of using [F-18]-labeled aryltrifluoroborates for PET tracers, but provides a chemical platform and a general approach for evaluating the stability of other aryltrifluoroborates. (c) 2008 Elsevier B.V. All rights reserved.},
	keywords = {ACIDS, aryltrifluoroborate, CROSS-COUPLING REACTIONS, KINETICS, PET, SYNTHESIS, [F-18]-labeling},
	isbn = {0022-1139},
	url = {<Go to ISI>://000255990600005},
	author = {Ting, R. and Lo, J. and Adam,Michael J. and Ruth, T. J. and Perrin,David M.}
}
@article {2289,
	title = {Capturing aqueous [F-18]-fluoride with an arylboronic ester for PET: Synthesis and aqueous stability of a fluorescent [F-18]-labeled aryltrifluoroborate},
	journal = {Journal of Fluorine Chemistry},
	volume = {129},
	number = {5},
	year = {2008},
	note = {ISI Document Delivery No.: 302SWTimes Cited: 5Cited Reference Count: 12Ting, Richard Lo, Justin Adam, Michael J. Ruth, Thomas J. Perrin, David M.},
	month = {May},
	pages = {349-358},
	type = {Article},
	abstract = {The aqueous stability of aryltrifluoroborates is of importance to their use in transition metal mediated coupling reactions as well as their potential use in [F-18]-labeled aryltrifluoroborate PET imaging agents. Nevertheless, few studies have fully characterized the solvolysis of fluoride from an aryltrifluoroborate in water. Using [F-19] NMR, fluorescence and [F-18]-labeling techniques, we disclose the composition of an aryltrifluoroborate of exceptional kinetic stability with respect to solvolytic defluoridation. This work not only highlights the potential of using [F-18]-labeled aryltrifluoroborates for PET tracers, but provides a chemical platform and a general approach for evaluating the stability of other aryltrifluoroborates. (c) 2008 Elsevier B.V. All rights reserved.},
	keywords = {ACIDS, aryltrifluoroborate, CROSS-COUPLING REACTIONS, KINETICS, PET, SYNTHESIS, [F-18]-labeling},
	isbn = {0022-1139},
	url = {<Go to ISI>://000255990600005},
	author = {Ting, R. and Lo, J. and Adam,Michael J. and Ruth, T. J. and Perrin,David M.}
}
