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- •Contents
- •List of Contributors
- •Foreword
- •Preface
- •Abbreviations
- •1.1 INTRODUCTION
- •1.7 SUMMARY
- •REFERENCES
- •2.1 INTRODUCTION
- •2.2 THERANOSTICS
- •REFERENCES
- •3.1 INTRODUCTION
- •3.3 68Ge/68Ga GENERATORS
- •REFERENCES
- •4.1 INTRODUCTION
- •4.2 TECHNETIUM-99m
- •4.3 IODINE-131
- •4.4 XENON-133
- •4.5 CYCLOTRON-PRODUCED RADIONUCLIDES
- •4.6 THALLIUM-201
- •4.7 GALLIUM-67
- •4.8 INDIUM-111
- •4.9 IODINE-123
- •4.A. APPENDIX
- •REFERENCES
- •5.1 INTRODUCTION
- •5.7 SUMMARY
- •7.1 INTRODUCTION
- •REFERENCES
- •8.1 INTRODUCTION
- •9.1 INTRODUCTION
- •10.2 Cu-MEDIATED RADIOFLUORINATION
- •10.3 Cu-MEDIATED HEAVY HALIDE RADIOHALOGENATION
- •10.4 CONCLUSIONS
- •REFERENCES
- •11.1 INTRODUCTION
- •REFERENCES
- •12.1 INTRODUCTION
- •12.3 MYOCARDIAL IMAGING AGENTS
- •12.5 BRAIN IMAGING AGENTS
- •12.6 RENAL IMAGING AGENTS
- •12.7 BONE IMAGING AGENTS
- •12.9 SENTINEL LYMPH NODE IMAGING AGENTS
- •12.12 CONCLUDING REMARKS
- •13.1 INTRODUCTION
- •13.2 EARLY RADIOCHEMISTRY SYNTHESIS MODULES
- •13.3 MODERN CASSETTE-BASED MODULES
- •13.5 HYBRID MODULES
- •13.6 MICROFLUIDIC SYSTEMS
- •13.8 AUTOMATED QUALITY CONTROL TESTING
- •REFERENCES
- •14.1 OVERVIEW
- •14.4 DRIVERS OF AUTOMATED QC
- •14.5 BARRIERS TO QC AUTOMATION
- •14.6 QC INNOVATION

111. Wilson, A.A., DaSilva, J.N., and Houle, S. (1996). Solid-phase radiosynthesis of [11C]
WAY 100635. J. Labelled Compd. Radiopharm. 38 (2): 149–154.
112. Cleij, M.C., Clark, J.C., Baron, J.-C., and Aigbirhio, F.I. (2007). Rapid preparation of
11
[
C]umazenil: captive solvent synthesis combined with purication by analytical
sized columns. J. Labelled Compd. Radiopharm. 50 (1): 19–24.
113. Maclean, D., Zhu, J., Chen, M. etal. (2003). Safety-catch linker strategies for the production of radiopharmaceuticals labeled with positron-emitting isotopes. J. Am.
Chem. Soc. 125 (34): 10168–10169.
114. Boudjemeline, M., Hopewell, R., Rochon, P.-L. etal. (2017). Highly ecient solid
phase supported radiosynthesis of [
11
C]PiB using TC18 cartridge as a “3-in-1” produc-
tion entity. J. Labelled Compd. Radiopharm. 60 (14): 632–638.
115. Herth, M.M., Thorpe, M.R., and Ferrieri, R.A. (2005). Synthesis of the phytohormone
11
[
C]methyl jasmonate via methylation on a C18 Sep Pak cartridge. J. Labelled Compd.
Radiopharm. 48 (5): 379–386.
116. Lodi, F., Trespidi, S., Di Pierro, D. etal. (2007). A simple tracerlab module modication
for automated on-column [
11
C]methylation and [11C]carboxylation. Appl. Radiat. Isot.
65 (6): 691–695.
117. Pascali, C., Bogni, A., Iwata, R. etal. (1999). High eciency preparation of L-[Smethyl-
11
C]methionine by on-column [11C]methylation on C18 Sep-Pak. J. Labelled
Compd. Radiopharm. 42 (8): 715–724.
118. Pascali, C., Bogni, A., Itawa, R. etal. (2000). [
cartridge: a convenient way to produce [N-methyl-
11
C]Methylation on a C18 Sep-Pak
11
C]choline. J. Labelled Compd.
Radiopharm. 43 (2): 195–203.
119. Hockley, B.G., Henderson, B., and Shao, X. (2012). Synthesis of [
11
([
C]CHL). In: Radiochemical Syntheses (eds. P.J.H. Scott and B.G. Hockley), 167–175.
11
C]choline chloride
Hoboken, NJ, USA: Wiley.
120. Wilson, A.A., Garcia, A., Bell, T. etal. (2001). Further progress on a remarkably simple
captive solvent method for [
11
C]-methylations. J. Labelled Compd. Radiopharm. 44
(S1): S999–S1001.
121. Studenov, A.R., Jivan, S., Adam, M.J. etal. (2004). Studies of the mechanism of the
in-loop synthesis of radiopharmaceuticals. Appl. Radiat. Isot. 61 (6): 1195–1201.
122. Iwata, R., Pascali, C., Bogni, A. etal. (2001). A simple loop method for the automated
preparation of [
11
C]raclopride from [11C]methyl triate. Appl. Radiat. Isot. 55 (1): 17–22.
123. Iwata, R., Pascali, C., Bogni, A. etal. (2002). A combined loop-SPE method for
the automated preparation of [
11
C]doxepin. J. Labelled Compd. Radiopharm. 45
(4): 271–280.
124. Wilson, A.A., Garcia, A., Houle, S., and Vasdev, N. (2009). Utility of commercial radiosynthetic modules in captive solvent [
11
C]-methylation reactions. J. Labelled Compd.
Radiopharm. 52 (11): 490–492.
125. Shao, X. and Kilbourn, M.R. (2009). A simple modication of GE tracerlab FX C pro for
rapid sequential preparation of [
11
C]carfentanil and [11C]raclopride. Appl. Radiat. Isot.
67 (4): 602–605.
225

126. Holt, D.P., Ravert, H.T., Dannals, R.F., and Pomper, M.G. (2006). Synthesis of [11C]
getinib for imaging epidermal growth factor receptor tyrosine kinase with positron
emission tomography. J. Labelled Compd. Radiopharm. 49 (10): 883–888.
127. Verdurand, M., Bort, G., Tadino, V. etal. (2008). Automated radiosynthesis of the
Pittsburg compound-B using a commercial synthesizer. Nucl. Med. Commun. 29
(10): 920–926.
128. Shao, X., Schnau, P.L., Fawaz, M.V., and Scott, P.J.H. (2013). Enhanced radiosyntheses
11
of [
C]raclopride and [11C]DASB using ethanolic loop chemistry. Nucl. Med. Biol. 40
(1): 109 –116.
129. Wilson, A.A., Garcia, A., Chestakova, A. etal. (2004). A rapid one-step radiosynthesis of the β -amyloid imaging radiotracer N-methyl-[
6-hydroxybenzothiazole ([
11
C]-6-OH-BTA-1). J. Labelled Compd. Radiopharm. 47
11
C]2-(4′-methylaminophenyl)-
(10): 679–682.
130. Gómez, V., Gispert, J.D., Amador, V., and Llop, J. (2008). New method for routine
production of L-[methyl-
11
C]methionine in loop synthesis. J. Labelled Compd. Radio-
pharm. 51 (1): 83–86.
131. Studenov, A.R., Jivan, S., Buckley, K.R., and Adam, M.J. (2003). Ecientin-loop synthesis of high specic radioactivity [
11
C]carfentanil. J. Labelled Compd. Radiopharm.
46 (9): 837–842.
132. Moran, M.D., Wilson, A.A., Stableford, W.T. etal. (2011). A rapid one-step radiosynthesis of [
11
C]-D-threo-methylphenidate. J. Labelled Compd. Radiopharm. 54
(3): 168–170.
133. Burton, T.J., Mackenzie, I.S., Balan, K. etal. (2012). Evaluation of the sensitivity and
specicity of (11)C-metomidate positron emission tomography (PET)-CT for lateralizing aldosterone secretion by Conn’s adenomas. J. Clin. Endocrinol. Metab. 97
(1): 100–109.
134. Rensch, C., Jackson, A., Lindner, S. etal. (2013). Microuidics: a groundbreaking technology for PET tracer production? Molecules 18 (7): 7930–7956.
135. Wang, M.-W., Lin, W.-Y., Liu, K. etal. (2010). Microuidics for positron emission
tomography probe development. Mol. Imaging 9 (4): 7290.2010.00027.
136. Miller, P.W. (2009). Radiolabelling with short-lived PET (positron emission tomography) isotopes using microuidic reactors. J. Chem. Technol. Biotechnol. 84
(3): 309–315.
137. Audrain, H. (2007). Positron emission tomography (PET) and microuidic devices: a
breakthrough on the microscale? Angew. Chemie Int. Ed. 46 (11): 1772–1775.
138. Lu, S.-Y., Watts, P., Chin, F.T. etal. (2004). Syntheses of
11
C- and 18F-labeled carboxylic
esters within a hydrodynamically-driven micro-reactor. Lab Chip 4 (6): 523.
139. Ungersboeck, J., Philippe, C., Haeusler, D. etal. (2012). Optimization of [
11
C]DASBsynthesis: vessel-based and ow-through microreactor methods. Appl. Radiat. Isot.
70 (11): 2615–2620.
140. Kawashima, H., Kimura, H., Nakaya, Y. etal. (2015). Application of microreactor to the
preparation of C-11-labeled compounds via O-[
synthesis of [
11
C]raclopride. Chem. Pharm. Bull. 63 (9): 737–740.
11
C]methylation with [11C]CH3I: rapid
226 Handbook of Radiopharmaceuticals

141. Haroun, S., Sanei, Z., Jivan, S. etal. (2013). Continuous-ow synthesis of [11C]raclopride, a positron emission tomography radiotracer, on a microuidic chip. Can. J.
Chem. 91 (5): 326–332.
142. Passchier, J. (2009). Fast high performance liquid chromatography in PET quality control and metabolite analysis. Q. J. Nucl. Med. Mol. imaging 53 (4): 411–416.
143. Zheng, Q.-H. and Mock, B.H. (2005). Purication of carbon-11 PET radiotracers
from unlabeled precursors by preparative HPLC and SPE. Biomed. Chromatogr. 19
(9): 671–676.
144. Lehel, S., Madsen, J., and Gillings, N. (2009). HPLC methods for the purication of
11
[
C]-labelled radiopharmaceuticals: reversal of the retention order of products and
precursors. J. Labelled Compd. Radiopharm. 52 (5): 177–181.
145. Nakao, R., Ito, T., Hayashi, K. etal. (2009). Rapid and ecient purication of positron
emission tomography probes by hydrophilic interaction chromatography. J. Chro-
matogr. A 1216 (18): 3933–3940.
146. Nics, L., Steiner, B., Klebermass, E.-M. etal. (2018). Speed matters to raise molar
radioactivity: fast HPLC shortens the quality control of C-11 PET-tracers. Nucl. Med.
Biol. 57: 28–33.
147. Shetty, H.U., Morse, C.L., Zhang, Y., and Pike, V.W. (2013). Characterization of fastdecaying PET radiotracers solely through LC-MS/MS of constituent radioactive and
carrier isotopologues. EJNMMI Res. 3 (1): 3.
148. Ram, S. and Lee Ehrenkaufer, R. (1988). Synthesis of
direct xation of [
11
C]carbon dioxide and [11C]carbon monoxide. Int. J. Radiat. Appl.
11
C-radiopharmaceuticals using
Instrum. B Nucl. Med. Biol. 15 (4): 345–355.
149. Tang, X., Tang, G., and Nie, D. (2013). Fully automated synthesis of
11
C-acetate as
tumor PET tracer by simple modied solid-phase extraction purication. Appl.
Radiat. Isot. 82: 81–86.
150. Pike, V.W., Eakins, M.N., Allan, R.M., and Selwyn, A.P. (1981). Preparation of carbon-11
labelled acetate and palmitic acid for the study of myocardial metabolism by emission-computerised axial tomography. J. Radioanal. Chem. 64 (1–2): 291–297.
151. Aubert, C., Huard-Perrio, C., and Lasne, M.-C. (1997). Rapid synthesis of aliphatic
amides by reaction of carboxylic acids, grignard reagent and amines: application to
the preparation of [
11
C]amides. J. Chem. Soc. Perkin Trans. 1 0 (19): 2837–2842.
152. Perrio-Huard, C., Aubert, C., and Lasne, M.-C. (2000). Reductive amination of
carboxylic acids and [
11
C]magnesium halide carboxylates. J. Chem. Soc. Perkin Trans. 1
0 (3): 311–316.
153. Mäding, P., Zessin, J., Pleiß, U. etal. (2006). Synthesis of a
derivative by [1-
11
C]acetylation. J. Labelled Compd. Radiopharm. 49 (4): 357–365.
154. Zhu, Y.C., Prenant, C., Crouzel, C. etal. (1992). Synthesis of [
11
C-labelled taxane
11
C]-ohmefentanyl, a
novel, highly potent and selective agonist for opiate μ-receptors. J. Labelled Compd.
Radiopharm. 31 (11): 853–860.
155. Plisson, C., Huiban, M., Pampols-Maso, S. etal. (2012). Automated preparation of
the dopamine D2/3 receptor agonist ligand [
11
C]-(+)-PHNO for human PET imaging
studies. Appl. Radiat. Isot. 70 (2): 380–387.
227

156. Matarrese, M., Sudati, F., Soloviev, D. etal. (2002). Automation of [11C]Acyl chloride
syntheses using commercially available
11
C-modules. Applied Radiation and Isotopes
57: 675–679.
157. Hwang, D.-R., Simpson, N.R., Montoya, J. etal. (1999). An improved one-pot
procedure for the preparation of [
11
C-carbonyl]-WAY100635. Nucl. Med. Biol. 26
(7): 815–819.
158. Luthra, S.K., Pike, V.W., and Brady, F. (1985). The preparation of carbon-11 labelled
diprenorphine: a new radioligand for the study of the opiate receptor system in vivo.
J. Chem. Soc., Chem. Commun. 0 (20): 1423.
159. Ben-David, I., Rozen, Y., Ortu, G., and Mishani, E. (2003). Radiosynthesis of ML03,
a novel positron emission tomography biomarker for targeting epidermal growth
factor receptor via the labeling synthon: [
11
C]acryloyl chloride. Appl. Radiat. Isot. 58
(2): 209–217.
160. Pekošak, A., Filp, U., Rotteveel, L. etal. (2015). Improved synthesis and application
11
of [
C]benzyl iodide in positron emission tomography radiotracer production. J.
Labelled Compd. Radiopharm. 58 (8): 342–348.
161. Berger, G., Maziere, M., Prenant, C., and Comar, D. (1980). Synthesis of carbon-11-labelled acetone. Int. J. Appl. Radiat. Isot. 31 (9): 577–578.
162. Studenov, A.R., Berridge, M.S., Soloviev, D.V. etal. (1999). High yield synthesis of
11
[
C]-acetone through selective quenching of methyl lithium. Nucl. Med. Biol. 26
(4): 431–435.
163. van der Meij, M., Carruthers, N.I., Herscheid, J.D.M. etal. (2003). Reductive N-alkylation of secondary amines with [2-
11
C]acetone. J. Labelled Compd. Radiopharm. 46 (11):
1075–1085.
164. Berger, G., Prenant, C., Sastre, J. etal. (1983). Synthesis of a β-blocker for heart visualization: [
165. Prenant, C., Sastre, J., Crouzel, C., and Syrota, A. (1987). Synthesis of
11
C]practolol. Int. J. Appl. Radiat. Isot. 34 (11): 1556–1557.
11
C-pindolol. J.
Labelled Compd. Radiopharm. 24 (2): 227–232.
166. Schou, M., Varnäs, K., Jucaite, A. etal. (2013). Radiolabeling of the cannabinoid
receptor agonist AZD1940 with carbon-11 and PET microdosing in non-human primate. Nucl. Med. Biol. 40 (3): 410–414.
167. Schou, M. and Halldin, C. (2012). Radiolabeling of two
and their application in the preparation of [
11
C]benzimidazole. J. Labelled Compd.
11
C-labeled formylating agents
Radiopharm. 55 (13): 460–462.
168. Chakraborty, P.K., Mangner, T.J., and Chugani, H.T. (1997). The synthesis of no-carrier-added [
11
C]urea from [11C]carbon dioxide and application to [11C]uracil synthesis.
Appl. Radiat. Isot. 48 (5): 619–621.
169. van Tilburg, E.W., Windhorst, A.D., van der Mey, M., and Herscheid, J.D.M. (2006).
One-pot synthesis of [
11
C]ureas via triphenylphosphinimines. J. Labelled Compd.
Radiopharm. 49 (4): 321–330.
170. Del Vecchio, A., Caillé, F., Chevalier, A. etal. (2018). Late-stage isotopic carbon
labeling of pharmaceutically relevant cyclic ureas directly from CO
. Angew. Chemie
2
Int. Ed. 57 (31): 9744–9748.
228 Handbook of Radiopharmaceuticals

171. Ram, S., Ehrenkaufer, R.E., and Jewett, D.M. (1986). Rapid reductive-carboxylation
of secondary amines, one pot synthesis of N′-(4-
11
C-methyl)imipramine. Int. J. Radiat.
Appl. Instrum. A Appl. Radiat. Isot. 37 (5): 391–395.
172. Ram, S. and Spicer, L.D. (1989). Synthesis of
11
from [
C]carbon dioxide. Int. J. Radiat. Appl. Instrum. A Appl. Radiat. Isot. 40
11
C-labeled chlorpromazine directly
(5): 413–416.
173. Ram, S., Ehrenkaufer, R.E., and Spicer, L.D. (1989). Synthesis of the labeled D1
receptor antagonist SCH 23390 using [
11
C]carbon dioxide. Int. J. Radiat. Appl. Instrum.
A Appl. Radiat. Isot. 40 (5): 425–427.
174. Ram, S. and Spicer, L.D. (1989). Direct incorporation of [
labeling bioactive molecules. An application to [
11
C]carbon dioxide for
11
C] labeled tamoxifen. J. Labelled
Compd. Radiopharm. 27 (6): 661–668.
175. Liger, F., Eijsbouts, T., Cadarossanesaib, F. etal. (2015). Direct [
amines from [
11
C]CO2 for the synthesis of PET radiotracers. Eur. J. Org. Chem. 2015
11
C]methylation of
(29): 6434–6438.
176. Schirbel, A., Holschbach, M.H., and Coenen, H.H. (1999). N.C.A.[
11
C]CO2 as a safe
substitute for phosgene in the carbonylation of primary amines. J. Labelled Compd.
Radiopharm. 42 (6): 537–551.
177. Hooker, J.M., Reibel, A.T., Hill, S.M. etal. (2009). One-pot, direct incorporation of
11
[
C]CO2 into carbamates. Angew. Chemie Int. Ed. 48 (19): 3482–3485.
178. Wilson, A.A., Garcia, A., Houle, S., and Vasdev, N. (2010). Direct xation of [
by amines: formation of [
11
C-carbonyl]-methylcarbamates. Org. Biomol. Chem. 8
11
C]-CO2
(2): 428–432.
179. Hooker, J.M., Kim, S.W., Alexo, D. etal. (2010). Histone deacetylase inhibitor MS-275
exhibits poor brain penetration: pharmacokinetic studies of [
11
C]MS-275 using posi-
tron emission tomography. ACS Chem. Neurosci. 1 (1): 65–73.
180. Wilson, A.A., Garcia, A., Houle, S. etal. (2011). Synthesis and application of isocyanates radiolabeled with carbon-11. Chem. Eur. J. 17 (1): 259–264.
181. Vasdev, N., Sadovski, O., Garcia, A. etal. (2011). Radiosynthesis of [
11
[
C]CO2 xation for imaging monoamine oxidase B. J. Labelled Compd. Radiopharm.
11
C]SL25.1188 via
54 (10): 678–680.
182. Kawamura, K., Hashimoto, H., Ogawa, M. etal. (2013). Synthesis, metabolite analysis,
and in vivo evaluation of [
11
C]Irinotecan as a novel positron emission tomography
(PET) probe. Nucl. Med. Biol. 40 (5): 651–657.
183. Wilson, A.A., Hicks, J.W., Sadovski, O. etal. (2013). Radiosynthesis and evaluation of
11
[
C-carbonyl]-labeled carbamates as fatty acid amide hydrolase radiotracers for pos-
itron emission tomography. J. Med. Chem. 56 (1): 201–209.
184. Hicks, J.W., Parkes, J., Tong, J. etal. (2014). Radiosynthesis and ex vivo evaluation of
11
[
C-carbonyl]carbamate- and urea-based monoacylglycerol lipase inhibitors. Nucl.
Med. Biol. 41 (8): 688–694.
185. Hicks, J.W., Wilson, A.A., Rubie, E.A. etal. (2012). Towards the preparation of radiolabeled 1-Aryl-3-benzyl ureas: radiosynthesis of [
11
C-carbonyl] AR-A014418 by [11C]CO2
xation. Bioorg. Med. Chem. Lett. 22 (5): 2099–2101.
229

186. Hicks, J.W., Parkes, J., Sadovski, O. etal. (2013). Synthesis and preclinical evaluation
11
of [
C-carbonyl]PF-04457845 for neuroimaging of fatty acid amide hydrolase. Nucl.
Med. Biol. 40 (6): 740–746.
187. Mossine, A.V., Brooks, A.F., Jackson, I.M. etal. (2016). Synthesis of diverse
PET radiotracers via direct incorporation of [
11
C]CO2. Bioconjugate Chem. 27 (5):
11
C-labeled
1382–1389.
188. Boileau, I., Bloomeld, P.M., Rusjan, P. etal. (2014). Whole-body radiation dosimetry
11
of
C-carbonyl-URB694: a PET tracer for fatty acid amide hydrolase. J. Nucl. Med. 55
(12): 1993–1997.
189. Rusjan, P.M., Wilson, A.A., Miler, L. etal. (2014). Kinetic modeling of the monoamine
oxidase B radioligand [
11
C]SL25.1188 in human brain with high-resolution positron
emission tomography. J. Cereb. Blood Flow Metab. 34 (5): 883–889.
190. Dahl, K., Collier, T.L., Cheng, R. etal. (2018). “In-Loop” [
11
C]CO2 xation: prototype
and proof of concept. J. Labelled Compd. Radiopharm. 61 (3): 252–262.
191. Dheere, A., Bongarzone, S., Taddei, C. etal. (2015). Synthesis of
rical ureas via the rapid incorporation of [
11
C]CO2 into aliphatic and aromatic amines.
11
C-labelled symmet-
Synlett 26 (16): 2257–2260.
192. Haji Dheere, A.K., Yusuf, N., and Gee, A. (2013). Rapid and ecient synthesis of [
ureas via the incorporation of [
11
C]CO2 into aliphatic and aromatic amines. Chem.
11
C]
Commun. 49 (74): 8193.
193. Bongarzone, S., Runser, A., Taddei, C. etal. (2017). From [
11
C]CO2 to [11C]amides: a rapid
one-pot synthesis via the Mitsunobu reaction. Chem. Commun. 53 (38): 5334–5337.
194. Downey, J., Bongarzone, S., Hader, S., and Gee, A.D. (2018). In-loop ow [
tion and radiosynthesis of N,N′-[
11
C]dibenzylurea. J. Labelled Compd. Radiopharm. 61
11
C]CO2 xa-
(3): 263–271.
195. Riss, P.J., Lu, S., Telu, S. etal. (2012). CuI-catalyzed
esters: a rapid and convenient entry to
11
C-labeled carboxylic acids, esters, and
11
C carboxylation of boronic acid
amides. Angew. Chemie Int. Ed. 51 (11): 2698–2702.
196. Rotstein, B.H., Hooker, J.M., Woo, J. etal. (2014). Synthesis of [
mediated [
11
C]carbon dioxide xation and preliminary PET imaging. ACS Med. Chem.
11
C]bexarotene by Cu-
Lett. 5 (6): 668–672.
197. Raque, W., Khanapur, S., Spilhaug, M.M., and Riss, P.J. (2017). Reaching out for
sensitive evaluation of the Mu opioid receptor in vivo: positron emission tomography
imaging of the agonist [
11
C]AH7921. ACS Chem. Neurosci. 8 (9): 1847–1852.
198. Jensen, C.H., Hansen, H.D., Bay, T. etal. (2017). Radiosynthesis and evaluation of
11
[
C]3-hydroxycyclopent-1-enecarboxylic acid as potential PET ligand for the high-
anity γ-hydroxybutyric acid binding sites. ACS Chem. Neurosci. 8 (1): 22–27.
199. Schoenberg, A., Bartoletti, I., and Heck, R.F. (1974). Palladium-catalyzed carboalkoxylation of aryl, benzyl, and vinylic halides. J. Org. Chem. 39 (23): 3318–3326.
200. Schoenberg, A. and Heck, R.F. (1974). Palladium-catalyzed amidation of aryl, heterocyclic, and vinylic halides. J. Org. Chem. 39 (23): 3327–3331.
201. Andersson, Y. and Långström, B. (1995). Synthesis of
ylative coupling reactions using [
11
C]carbon monoxide. J. Chem. Soc. Perkin Trans. 1 0
11
C-labelled ketones via carbon-
(4): 287–289.
230 Handbook of Radiopharmaceuticals

202. Al-Qahtani, M.H. and Pike, V.W. (2000). Rapid mild syntheses of [11C]benzophenones
by Pd(0)-catalysed
11
C-carbonylative coupling of Iodoarenes with phenyltributylstan-
nane in DME-water. J. Labelled Compd. Radiopharm. 43 (8): 825–835.
203. Al-Qahtani, M.H. and Pike, V.W. (2000). Palladium(II)-mediated
11
C-carbonylative coupling of diaryliodonium salts with organostannanes—a new, mild and rapid synthesis
of aryl [
204. Lidström, P., Kihlberg, T., and Långström, B. (1997). [
dium-mediated synthesis of
11
C]ketones. J. Chem. Soc. Perkin Trans. 1 0 (6): 1033–1036.
11
C]carbon monoxide in the palla-
11
C-labelled ketones. J. Chem. Soc. Perkin Trans. 1 0 (18):
2701–2706.
205. Nader, M. and Oberdorfer, F. (2002). Syntheses of [Carbonyl(2-Benzoylphenoxy)-N-phenylacetamide from [
11
C]carbon monoxide by the suzuki
11
C]2-
and the stille reactions. Appl. Radiat. Isot. 57 (5): 681–685.
206. Rahman, O. (2015). [
11
C]carbon monoxide in labeling chemistry and positron emission
tomography tracer development: scope and limitations. J. Labelled Compd. Radio-
pharm. 58 (3): 86–98.
207. Kihlberg, T., Langstrom, B., Ferm, T., and Eriksson, J. (2008). Methods and apparatus
for production and use of
11
C-carbon monoxide in labeling synthesis. US patent appli-
cation 20080095693.
208. Itsenko, O., Kihlberg, T., and Långström, B. (2006). Labeling of aliphatic carboxylic
acids using [
209. Långström, B., Itsenko, O., and Rahman, O. (2007). [
11
C]carbon monoxide. Nat. Protoc. 1 (2): 798–802.
11
C]carbon monoxide, a versatile
and useful precursor in labelling chemistry for PET-ligand development. J. Labelled
Compd. Radiopharm. 50 (9–10): 794–810.
210. Hostetler, E.D. and Burns, H.D. (2002). A remote-controlled high pressure reactor for
radiotracer synthesis with [
211. Kihlberg, T. and Långström, B. (1999). Biologically active
ladium-mediated reactions with aryl halides and [
11
C]carbon monoxide. Nucl. Med. Biol. 29 (8): 845–848.
11
C-labeled amides using pal-
11
C]carbon monoxide. J. Org. Chem.
64 (25): 9201–9205.
212. Dahl, K. and Nordeman, P. (2017).
11
C-benzoyl chlorides with tetrabutylammonium chloride as chloride source. Eur. J.
11
C-carbonylation through in situ generated
Org. Chem. 2017 (18): 2648–2651.
213. Roslin, S., Dahl, K., and Nordeman, P. (2018). Reaction of
metalloid reagents:
ketones from [
11
C-labeling of benzyl alcohols, benzaldehydes, and phenyl
11
C]CO. J. Labelled Compd. Radiopharm. 61 (5): 447–454.
214. Altomonte, S., Telu, S., Lu, S., and Pike, V.W. (2017). Pd(0)-mediated
of aryl(Mesityl)iodonium salts as a route to [
11
C]arylcarboxylic acids and derivatives.
11
C-benzoyl chlorides with
11
C-carbonylation
J. Org. Chem. 82 (22): 11925–11932.
215. Kealey, S., Gee, A., and Miller, P.W. (2014). Transition metal mediated [
11
C]carbonylation reactions: recent advances and applications. J. Labelled Compd. Radiopharm. 57
(4): 195–201.
216. Hong, J., Lu, S., Xu, R. etal. (2015). [Carbonyl[methylamino]pyrimidin-4-Yl)thiazol-2-Yl)benzamide ([
11
C]4-Fluoro-N-methyl-N-(4-(6-
11
C]FIMX) is an eective radioligand for PET imaging of metabotropic glutamate receptor 1 (MGluR1) in monkey
brain. Nucl. Med. Biol. 42 (12): 967–974.
231

217. Rahman, O., Kihlberg, T., and Långström, B. (2002). Synthesis of N-methyl-N(1-methylpropyl)-1-(2-chlorophenyl)isoquinoline-3-[
PK11195) and some analogues using [
11
C]carbon monoxide and 1-(2-chlorophenyl)
11
C]carboxamide ([11C-carbonyl]
isoquinolin-3-yl triate. J. Chem. Soc. Perkin Trans. 1 0 (23): 2699–2703.
218. Rahman, O. and Långström, B. (2007). Synthesis of N-(2,5-dimethoxybenzyl)-N(5-uoro-2-phenoxyphenyl)[carbonylanalogues using [
11
C]carbon monoxide and palladium(0) complex. J. Labelled Compd.
11
C]acetamide ([carbonyl-11C]DAA1106) and
Radiopharm. 50 (13): 1192–1199.
219. Åberg, O., Lindhe, Ö., Hall, H. etal. (2009). Synthesis and biological evaluation of
[carboxyl-
220. Nordeman, P., Estrada, S., Odell, L.R. etal. (2014).
11
C]eprosartan. J. Labelled Compd. Radiopharm. 52 (8): 295–303.
11
C-labeling of a potent hydroxyethylamine BACE-1 inhibitor and evaluation in vitro and in vivo. Nucl. Med. Biol. 41
(6): 536–543.
221. Siméon, F., Culligan, W., Lu, S., and Pike, V. (2017).
11
C-labeling of aryl ketones as
candidate histamine subtype-3 receptor PET radioligands through Pd(0)-mediated
11
C-carbonylative coupling. Molecules 22 (5): 792.
222. Lu, S., Zhang, Y., Kalin, J.H. etal. (2016). Exploration of the labeling of [
A at the hydroxamic acid site with [
11
C]carbon monoxide. J. Labelled Compd. Radio-
11
C]tubastatin
pharm. 59 (1): 9–13.
223. Hostetler, E., Sanabria, S., Krause, S. etal. (2006). Neuropeptide-Y Y5 (NPY5) receptor:
occupancy studies in rhesus monkey using a novel NPY5 PET tracer. Neuroimage 31: T16.
224. Burns, H.D., Gibson, R.E., Hamill, T.G., and Fukami, T. (2003). Radiolabeled neuropeptide Y Y5 receptor antagonists. International patent WO2003010175A2.
225. Erondu, N., Gantz, I., Musser, B. etal. (2006). Neuropeptide Y5 receptor antagonism
does not induce clinically meaningful weight loss in overweight and obese adults.
Cell Metab. 4 (4): 275–282.
226. Åberg, O. and Långström, B. (2012). Combinatorial synthesis of labelled drugs and PET
tracers: synthesis of a focused library of
11
C-carbonyl-labelled acrylamides as potential
biomarkers of EGFR expression. J. Labelled Compd. Radiopharm. 55 (14): 477–483.
227. Van der Wildt, B., Shen, B., and Chin, F.T. (2018). A [
11
C]CO dispensing system for
rapid screening of carbonylation reactions. J. Labelled Compd. Radiopharm. 61 (14):
1110 –1114.
228. Doi, H., Barletta, J., Suzuki, M. etal. (2004). Synthesis of
11
C-labelled N,N′-
diphenylurea and ethyl phenylcarbamate by a rhodium-promoted carbonylation via
11
[
C]Isocyanatobenzene using phenyl azide and [11C]carbon monoxide. Org. Biomol.
Chem. 2 (21): 3063–3066.
229. Barletta, J., Karimi, F., and Långström, B. (2006). Synthesis of [
ureas by a rhodium-mediated carbonylation reaction using [
11
C-carbonyl]hydroxy-
11
C]carbon monoxide. J.
Labelled Compd. Radiopharm. 49 (5): 429–436.
230. Ilovich, O., Åberg, O., Långström, B., and Mishani, E. (2009). Rhodium-mediated
11
[
C]carbonylation: a library of N-phenyl-N′-{4-(4-quinolyloxy)-phenyl}-[11C]-urea
derivatives as potential PET angiogenic probes. J. Labelled Compd. Radiopharm. 52
(5): 151–157.
232 Handbook of Radiopharmaceuticals

231. Åberg, O. and Långström, B. (2011). Synthesis of substituted [11C]Ureas and [11C]
sulphonylureas by Rh(I)-mediated carbonylation. J. Labelled Compd. Radiopharm. 54
(1): 38–42.
232. Barletta, J., Karimi, F., Doi, H., and Långström, B. (2006). Synthesis of diethyl [car-
11
bonyl-
C]malonate from [11C]carbon monoxide by rhodium-promoted carbonylation
and its application as a reaction intermediate. J. Labelled Compd. Radiopharm. 49
(9): 801–809.
233. Itsenko, O., Kihlberg, T., and Långström, B. (2004). Photoinitiated carbonylation
11
with [
C]carbon monoxide using amines and alkyl iodides. J. Org. Chem. 69 (13):
4356–4360.
234. Itsenko, O., Norberg, D., Rasmussen, T. etal. (2007). Radical carbonylation with [
11
C]
carbon monoxide promoted by oxygen-centered radicals: experimental and DFT
studies of the mechanism. J. Am. Chem. Soc. 129 (29): 9020–9031.
235. Itsenko, O., Kihlberg, T., and Långström, B. (2005). Synthesis of aliphatic [carbonyl-
11
C]esters using [11C]carbon monoxide. Eur. J. Org. Chem. 2005 (17): 3830–3834.
236. Itsenko, O. and Långström, B. (2005). Photoinitiated free radical carbonylation
enhanced by photosensitizers. Org. Lett. 7 (21): 4661–4664.
237. Itsenko, O. and Långström, B. (2005). Radical-mediated carboxylation of alkyl iodides
11
with [
C]carbon monoxide in solvent mixtures. J. Org. Chem. 70 (6): 2244–2249.
238. Itsenko, O., Kihlberg, T., and Långström, B. (2005). Carboxylation of alkyl iodides with
11
[
C] and (13C)carbon monoxide: using sulfoxides as oxygen nucleophiles. Synlett 2005
(20): 3154–3156.
239. Kihlberg, T., Karimi, F., and Långström, B. (2002). [
mediated synthesis of
11
C-carbamoyl compounds. J. Org. Chem. 67 (11): 3687–3692.
240. Audrain, H., Martarello, L., Gee, A., and Bender, D. (2004). Utilisation of [
11
C]Carbon monoxide in selenium-
11
C]-labelled
boron carbonyl complexes in palladium carbonylation reaction. Chem. Commun.
0 (5): 558.
241. Kealey, S., Miller, P.W., Long, N.J. etal. (2009). Copper(I) scorpionate complexes and
their application in palladium-mediated [
11
C]carbonylation reactions. Chem. Commun.
0 (25): 3696.
242. Jennings, L.E., Kealey, S., Miller, P.W. etal. (2011). N-heterocyclic carbenes as ligands
in palladium-mediated [
11
C]radiolabelling of [11C]amides for positron emission
tomography. J. Labelled Compd. Radiopharm. 54 (3): 135–139.
243. Buscemi, G., Miller, P.W., Kealey, S. etal. (2011). Rapid carbonylative coupling
reactions using palladium(i) dimers: applications to
11
CO-radiolabelling for the syn-
thesis of PET tracers. Org. Biomol. Chem. 9 (9): 3499.
244. Kealey, S., Plisson, C., Collier, T.L. etal. (2011). Microuidic reactions using [
11
C]carbon
monoxide solutions for the synthesis of a positron emission tomography radiotracer.
Org. Biomol. Chem. 9 (9): 3313.
245. Díaz, D.J., Darko, A.K., and McElwee-White, L. (2007). Transition metal-catalyzed
oxidative carbonylation of amines to ureas. Eur. J. Org. Chem. 2007 (27): 4453–4465.
246. Roslin, S., Brandt, P., Nordeman, P. etal. (2017). Synthesis of
11
C-labelled ureas by
palladium(II)-mediated oxidative carbonylation. Molecules 22 (10): 1688.
233

247. Takashima-Hirano, M., Ishii, H., and Suzuki, M. (2012). Synthesis of [11C]Am80 via novel
Pd(0)-mediated rapid [
11
C]carbonylation using arylboronate and [11 C]carbon mon-
oxide. ACS Med. Chem. Lett. 3 (10): 804–807.
11
C]carbon
11
C]
248. Ishii, H., Minegishi, K., Nagatsu, K., and Zhang, M.-R. (2015). Pd(0)-mediated [
carbonylation of aryl and heteroaryl boronic acid pinacol esters with [
monoxide under ambient conditions and a facile process for the conversion of [car-
11
bonyl-
249. Stevens, M.Y., Chow, S.Y., Estrada, S. etal. (2016). Synthesis of
C]esters to [carbonyl-11C]amides. Tetrahedron 71 (10): 1588–1596.
11
C-labeled sulfonyl
carbamates through a multicomponent reaction employing sulfonyl azides, alcohols,
11
and [
C]CO. ChemistryOpen 5 (6): 566–573.
250. Roslin, S., De Rosa, M., Deuther-Conrad, W. etal. (2017). Synthesis and in vitro evaluation of 5-substituted benzovesamicol analogs containing N-substituted amides as
potential positron emission tomography tracers for the vesicular acetylcholine transporter. Bioorg. Med. Chem. 25 (19): 5095–5106.
251. van der Wildt, B., Wilhelmus, M.M.M., Bijkerk, J. etal. (2016). Development of
carbon-11 labeled acryl amides for selective PET imaging of active tissue transglutaminase. Nucl. Med. Biol. 43 (4): 232–242.
252. Filp, U., Pees, A.L., Taddei, C. etal. (2017). Ecient synthesis of
11
C-acrylamides and their application in Michael addition reactions for PET tracer
11
C-acrylesters,
development. Eur. J. Org. Chem. 2017 (34): 5154–5162.
253. Chow, S.Y., Odell, L.R., and Eriksson, J. (2016). Low-pressure radical
11
C-aminocarbonylation of alkyl iodides through thermal initiation. Eur. J. Org. Chem. 2016 (36):
5980–5989.
254. Rahman, O., Långström, B., and Halldin, C. (2016). Alkyl iodides and [
11
C]CO in nickel-
mediated cross-coupling reactions: successful use of alkyl electrophiles containing
a β hydrogen atom in metal-mediated [
11
C]carbonylation. ChemistrySelect 1 (10):
2498–2501.
255. Martinelli, J.R., Freckmann, D.M.M., and Buchwald, S.L. (2006). Convenient method
for the preparation of Weinreb amides via Pd-catalyzed aminocarbonylation of aryl
bromides at atmospheric pressure. Org. Lett. 8 (21): 4843–4846.
256. Dahl, K., Schou, M., Amini, N., and Halldin, C. (2013). Palladium-mediated [
11
C]carbonylation at atmospheric pressure: a general method using xantphos as supporting
ligand. Eur. J. Org. Chem. 2013 (7): 1228–1231.
257. Dahl, K., Schou, M., Rahman, O., and Halldin, C. (2014). Improved yields for the palladium-mediated
11
C-carbonylation reaction using microwave technology. Eur. J. Org.
Chem. 2014 (2): 307–310.
258. Rahman, O., Takano, A., Amini, N. etal. (2015). Synthesis of ([
and a comparison with ([
11
C]methyl)raclopride in a monkey PET study. Nucl. Med. Biol.
11
C]carbonyl)raclopride
42 (11): 893–898.
259. Andersen, T.L., Friis, S.D., Audrain, H. etal. (2015). Ecient
11
C-carbonylation of isolated aryl palladium complexes for PET: application to challenging radiopharmaceutical synthesis. J. Am. Chem. Soc. 137 (4): 1548–1555.
234 Handbook of Radiopharmaceuticals
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