Journal of the American Chemical Society
Communication
(7) A related strategy for the preparation of [18F]aryl fluorides has been
documented. See: Lee, E.; Kamlet, A. S.; Powers, D. C.; Neumann, C.
N.; Boursalian, G. B.; Furuya, T.; Choi, D. C.; Hooker, J. M.; Ritter, T.
Science 2011, 334, 639.
the capability of 1−4 to produce oxidative addition complex A in
situ. As a consequence of the mild reaction conditions and
robustness of this methodology, it exhibits wide functional group
tolerance and is highly amenable for high-activity synthesis, even
of densely functionalized molecules.
(8) Lee, H. G.; Milner, P. J.; Colvin, M. T.; Andreas, L.; Buchwald, S. L.
Inorg. Chim. Acta 2014, 422, 188.
(9) To set up multiple experiments at a time, a stock solution of [11C]
HCN was used, although it could be directly introduced in a gaseous
form (vide infra).
ASSOCIATED CONTENT
* Supporting Information
■
S
(10) A variety of solvents, including Et2O, DMSO, acetone, and tert-
amyl alcohol, could be used to furnish the product in good RCC (see
Supporting Information Table S1).
Experimental details and compound characterization data. This
material is available free of charge via the Internet at http://pubs.
(11) Andersson, Y.; Langstrom, B. J. Chem. Soc., Perkin Trans. 1 1994,
̊
̈
1395.
AUTHOR INFORMATION
■
(12) Collins, K. D.; Glorius, F. Nat. Chem. 2013, 5, 597.
(13) Fleming, F. F.; Yao, L.; Ravikumar, P. C.; Funk, L.; Shook, B. C. J.
Med. Chem. 2010, 53, 7902.
Corresponding Authors
(14) Andersson, Y.; Bergstrom, M.; Langstrom, B. Appl. Radiat. Isot.
̊
̈
1994, 45, 707.
(15) Simeon, F.; Sobrio, F.; Gourand, F.; Barre,
Trans. 1 2001, 690.
Author Contributions
́
́
L. J. Chem. Soc., Perkin
∥H.G.L. and P.J.M. contributed equally.
Notes
(16) Ponchant, M.; Hinnen, F.; Demphel, S.; Crouzel, C. Appl. Radiat.
Isot. 1997, 48, 755.
(17) Dorell, K.; Cohen, M. A.; Huprikar, S. S.; Gorman, J. M.; Jones, M.
The authors declare the following competing financial interest:
MIT has obtained or has filed patents on some of the ligands/
precatalysts used in this work from which S.L.B. and former/
current co-workers receive royalty payments.
Psychosomatics 2005, 46, 91.
(18) Robinson, D. S.; Kajdasz, D. K.; Gallipoli, S.; Whalen, H.; Wamil,
A.; Reed, C. R. J. Clin. Psychopharmacol. 2011, 31, 643.
(19) Hanada, T.; Hashizume, Y.; Tokuhara, N.; Takenaka, O.;
Kohmura, N.; Ogasawara, A.; Hatakeyama, S.; Ohgoh, M.; Ueno, M.;
Nishizawa, Y. Epilepsia 2011, 52, 1331.
(20) Zheng, M.-Q.; Nabulsi, N.; Kim, S. J.; Tomasi, G.; Lin, S.-F.;
Mitch, C.; Quimby, S.; Barth, V.; Rash, K.; Masters, J.; Navarro, A.;
Seest, E.; Morris, E. D.; Carson, R. E.; Huang, Y. J. Nucl. Med. 2013, 54,
455.
(21) PET radiotracer administered doses vary but are generally 0.1−
0.3 mCi/kg (human), 0.1−0.5 mCi/kg (nonhuman primates), 1−5
mCi/kg (rodent) for 11C.
(22) ⟨823⟩ Positron Emission Tomography Drugs for Compounding,
Investigational, and Research Uses. United States Pharmacopeia and
National Formulary (USP 35-NF 30). 2012. United States Pharmaco-
peia Convention, Rockville, MD.
ACKNOWLEDGMENTS
■
Research reported in this publication was supported by the
National Institutes of Health (GM46059). A portion of this
research was carried out at the Athinoula A. Martinos Center for
Biomedical Imaging at the Massachusetts General Hospital,
using resources provided by the Center for Functional
Neuroimaging Technologies, P41EB015896, a P41 Regional
Resource supported by the National Institute of Biomedical
Imaging and Bioengineering (NIBIB), National Institutes of
Health. This work also involved the use of instrumentation
supported by the National Institutes of Health Shared
Instrumentation Grant Program and/or High-End Instrumenta-
tion Grant Program (S10RR017208 and S10RR026666). The
content is solely the responsibility of the authors and does not
necessarily represent the official views of the National Institutes
of Health. P.J.M. thanks the National Science Foundation for a
predoctoral fellowship (2010094243). We also thank Amgen for
an educational donation. M.S.P. thanks NIH-NIDA for a
postdoctoral fellowship (2T32DA015036). Technical assistance
from Nathaniel Schauer, Judit Sore, and Dr. Ramesh
Neelamegam (MGH/HST) is appreciated. We are grateful to
Dr. Todd Senecal (MIT) for performing preliminary experi-
ments.
REFERENCES
■
(1) Ametamey, S. M.; Honer, M.; Schubiger, P. A. Chem. Rev. 2008,
108, 1501.
̈
(2) Miller, P. W.; Long, N. J.; Vilar, R.; Gee, A. D. Angew. Chem., Int. Ed.
2008, 47, 8998.
(3) Alternatively, the less widely employed Rosenmund−von Braun
reaction can be used. See ref 2.
(4) Anbarasan, P.; Schareina, T.; Beller, M. Chem. Soc. Rev. 2011, 40,
5049.
(5) For example, a base induced loss of stereochemical integrity during
the radiosynthesis of a [11C]aryl nitrile has been reported: Donohue, S.
R.; Pike, V. W.; Finnema, S. J.; Truong, P.; Andersson, J.; Gulyas
́
, B.;
Halldin, C. J. Med. Chem. 2008, 51, 5608.
(6) Senecal, T. D.; Shu, W.; Buchwald, S. L. Angew. Chem., Int. Ed.
2013, 52, 10035.
D
J. Am. Chem. Soc. XXXX, XXX, XXX−XXX