Reactive Palladium–Ligand Complexes for 11C-Carbonylation at Ambient Pressure: A Breakthrough in Carbon-11 Chemistry
The Pd–Xantphos-mediated 11C-carbonylation protocol (also known as the “Xantphos- method”), due to its simplistic and convenient nature, has facilitated researchers in meeting a longstanding need for preparing 11C-carbonyl-labeled radiopharmaceuticals at ambient pressure for positron emission tomogr...
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| Published in | Pharmaceuticals (Basel, Switzerland) Vol. 16; no. 7; p. 955 |
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| Main Authors | , , , |
| Format | Journal Article |
| Language | English |
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03.07.2023
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| Abstract | The Pd–Xantphos-mediated 11C-carbonylation protocol (also known as the “Xantphos- method”), due to its simplistic and convenient nature, has facilitated researchers in meeting a longstanding need for preparing 11C-carbonyl-labeled radiopharmaceuticals at ambient pressure for positron emission tomography (PET) imaging and drug discovery. This development could be viewed as a breakthrough in carbon-11 chemistry, as evidenced by the rapid global adoption of the method by the pharmaceutical industry and academic laboratories worldwide. The method has been fully automated for the good manufacturing practice (GMP)-compliant production of novel radiopharmaceuticals for human use, and it has been adapted for “in-loop” reactions and microwave technology; an impressive number of 11C-labeled compounds (>100) have been synthesized. Given the simplicity and efficiency of the method, as well as the abundance of carbonyl groups in bioactive drug molecules, we expect that this methodology will be even more widely adopted in future PET radiopharmaceutical research and drug development. |
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| AbstractList | The Pd–Xantphos-mediated 11C-carbonylation protocol (also known as the “Xantphos- method”), due to its simplistic and convenient nature, has facilitated researchers in meeting a longstanding need for preparing 11C-carbonyl-labeled radiopharmaceuticals at ambient pressure for positron emission tomography (PET) imaging and drug discovery. This development could be viewed as a breakthrough in carbon-11 chemistry, as evidenced by the rapid global adoption of the method by the pharmaceutical industry and academic laboratories worldwide. The method has been fully automated for the good manufacturing practice (GMP)-compliant production of novel radiopharmaceuticals for human use, and it has been adapted for “in-loop” reactions and microwave technology; an impressive number of 11C-labeled compounds (>100) have been synthesized. Given the simplicity and efficiency of the method, as well as the abundance of carbonyl groups in bioactive drug molecules, we expect that this methodology will be even more widely adopted in future PET radiopharmaceutical research and drug development. The Pd-Xantphos-mediated 11C-carbonylation protocol (also known as the "Xantphos- method"), due to its simplistic and convenient nature, has facilitated researchers in meeting a longstanding need for preparing 11C-carbonyl-labeled radiopharmaceuticals at ambient pressure for positron emission tomography (PET) imaging and drug discovery. This development could be viewed as a breakthrough in carbon-11 chemistry, as evidenced by the rapid global adoption of the method by the pharmaceutical industry and academic laboratories worldwide. The method has been fully automated for the good manufacturing practice (GMP)-compliant production of novel radiopharmaceuticals for human use, and it has been adapted for "in-loop" reactions and microwave technology; an impressive number of 11C-labeled compounds (>100) have been synthesized. Given the simplicity and efficiency of the method, as well as the abundance of carbonyl groups in bioactive drug molecules, we expect that this methodology will be even more widely adopted in future PET radiopharmaceutical research and drug development.The Pd-Xantphos-mediated 11C-carbonylation protocol (also known as the "Xantphos- method"), due to its simplistic and convenient nature, has facilitated researchers in meeting a longstanding need for preparing 11C-carbonyl-labeled radiopharmaceuticals at ambient pressure for positron emission tomography (PET) imaging and drug discovery. This development could be viewed as a breakthrough in carbon-11 chemistry, as evidenced by the rapid global adoption of the method by the pharmaceutical industry and academic laboratories worldwide. The method has been fully automated for the good manufacturing practice (GMP)-compliant production of novel radiopharmaceuticals for human use, and it has been adapted for "in-loop" reactions and microwave technology; an impressive number of 11C-labeled compounds (>100) have been synthesized. Given the simplicity and efficiency of the method, as well as the abundance of carbonyl groups in bioactive drug molecules, we expect that this methodology will be even more widely adopted in future PET radiopharmaceutical research and drug development. The Pd–Xantphos-mediated 11 C-carbonylation protocol (also known as the “Xantphos- method”), due to its simplistic and convenient nature, has facilitated researchers in meeting a longstanding need for preparing 11 C-carbonyl-labeled radiopharmaceuticals at ambient pressure for positron emission tomography (PET) imaging and drug discovery. This development could be viewed as a breakthrough in carbon-11 chemistry, as evidenced by the rapid global adoption of the method by the pharmaceutical industry and academic laboratories worldwide. The method has been fully automated for the good manufacturing practice (GMP)-compliant production of novel radiopharmaceuticals for human use, and it has been adapted for “in-loop” reactions and microwave technology; an impressive number of 11 C-labeled compounds (>100) have been synthesized. Given the simplicity and efficiency of the method, as well as the abundance of carbonyl groups in bioactive drug molecules, we expect that this methodology will be even more widely adopted in future PET radiopharmaceutical research and drug development. |
| Author | Dahl, Kenneth Vasdev, Neil Lindberg, Anton Schou, Magnus |
| AuthorAffiliation | 3 Azrieli Centre for Neuro-Radiochemistry, Brain Health Imaging Centre, Centre for Addiction and Mental Health, 250 College St., Toronto, ON M5T1R8, Canada; anton.lindberg@camh.ca 4 Department of Psychiatry, University of Toronto, 250 College St., Toronto, ON M5T1R8, Canada 1 PET Science Centre, Precision Medicine and Biosamples, Oncology R&D, AstraZeneca, Karolinska Institutet, SE-17176 Stockholm, Sweden; magnus.schoul@astrazeneca.com 2 Department of Clinical Neuroscience, Centre for Psychiatry Research, Karolinska Institutet and Stockholm County Council, SE-17176 Stockholm, Sweden |
| AuthorAffiliation_xml | – name: 4 Department of Psychiatry, University of Toronto, 250 College St., Toronto, ON M5T1R8, Canada – name: 2 Department of Clinical Neuroscience, Centre for Psychiatry Research, Karolinska Institutet and Stockholm County Council, SE-17176 Stockholm, Sweden – name: 3 Azrieli Centre for Neuro-Radiochemistry, Brain Health Imaging Centre, Centre for Addiction and Mental Health, 250 College St., Toronto, ON M5T1R8, Canada; anton.lindberg@camh.ca – name: 1 PET Science Centre, Precision Medicine and Biosamples, Oncology R&D, AstraZeneca, Karolinska Institutet, SE-17176 Stockholm, Sweden; magnus.schoul@astrazeneca.com |
| Author_xml | – sequence: 1 givenname: Kenneth surname: Dahl fullname: Dahl, Kenneth – sequence: 2 givenname: Anton surname: Lindberg fullname: Lindberg, Anton – sequence: 3 givenname: Neil orcidid: 0000-0002-2087-5125 surname: Vasdev fullname: Vasdev, Neil – sequence: 4 givenname: Magnus surname: Schou fullname: Schou, Magnus |
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| Cites_doi | 10.1021/ol061902t 10.1002/chem.202100544 10.1007/s00280-011-1593-0 10.1186/s41181-019-0073-4 10.1021/jo801279r 10.1021/ml300160w 10.1021/acs.jmedchem.0c01053 10.1002/jlcr.3596 10.1002/chem.201002644 10.1021/ja511441u 10.1002/jlcr.3258 10.1002/jlcr.3872 10.1039/C7CY01629H 10.1021/acschemneuro.7b00493 10.1021/jo990616a 10.1002/anie.200900013 10.1002/jlcr.3866 10.1002/jlcr.3262 10.1021/cr0782426 10.1002/ejoc.201201708 10.1002/adsc.200900563 10.2967/jnumed.118.213223 10.1002/jlcr.1446 10.1021/acsomega.0c00524 10.3389/fnume.2021.772289 10.1016/j.nucmedbio.2015.07.003 10.1021/acs.jmedchem.8b00138 10.1021/cr9902704 10.3389/fmed.2022.812270 10.1002/anie.200901481 10.1148/radiol.2312021185 10.1021/acs.bioconjchem.6b00163 10.1021/acs.bioconjchem.7b00583 10.1002/anie.201700446 10.1021/ol503471e 10.1002/ejoc.200600700 10.1016/j.nucmedbio.2020.02.005 10.1002/jlcr.2930 10.1039/C5CC02095F 10.1039/b906166e 10.1016/j.cpet.2020.12.003 10.1002/anie.200800222 10.1002/jlcr.3150 10.1002/jlcr.3805 10.4155/fmc-2019-0329 10.1021/acs.chemrev.2c00398 10.1039/C8CC09661A 10.1016/j.nucmedbio.2016.01.003 10.3389/fnume.2021.820235 10.1039/b314982j 10.1002/jlcr.2981 |
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| References | ref_50 Toddei (ref_11) 2017; 61 Scott (ref_10) 2009; 48 Andersen (ref_38) 2015; 137 Wilhelmus (ref_36) 2016; 43 Kealey (ref_12) 2014; 57 Dahl (ref_31) 2020; 63 Itsenko (ref_19) 2007; 50 Martinelli (ref_26) 2006; 8 Wilson (ref_52) 2019; 60 Ferrat (ref_42) 2020; 63 Ferrat (ref_53) 2021; 21 Nerella (ref_5) 2022; 9 Kamer (ref_25) 2000; 100 Shegani (ref_9) 2023; 123 Eriksson (ref_15) 2021; 92 Neumann (ref_17) 2009; 48 Taddei (ref_14) 2019; 4 Cornilleau (ref_57) 2017; 28 Dahl (ref_16) 2013; 2013 Dahl (ref_30) 2013; 2014 ref_21 Ferrat (ref_40) 2020; 63 Andersen (ref_39) 2017; 56 Schwaiger (ref_4) 2005; 46 Audrain (ref_20) 2004; 10 Cornilleau (ref_56) 2015; 17 Miller (ref_29) 2011; 17 Luzi (ref_47) 2019; 12 Kihlberg (ref_18) 1999; 64 Lindberg (ref_32) 2021; 1 Rahman (ref_13) 2015; 58 Dahl (ref_45) 2018; 9 Kamer (ref_24) 2018; 8 Eriksson (ref_22) 2012; 55 ref_33 Taddei (ref_48) 2015; 51 Miller (ref_28) 2009; 351 Rahman (ref_46) 2015; 42 Antoni (ref_8) 2015; 58 Narayanaswami (ref_44) 2021; 2 Simon (ref_55) 2011; 68 Mossine (ref_37) 2016; 27 Zmuda (ref_51) 2018; 61 Halldin (ref_2) 2001; 45 Martinelli (ref_27) 2008; 73 Eriksson (ref_34) 2007; 2007 Duffy (ref_43) 2020; 5 Donnelly (ref_41) 2022; 1 Ametamey (ref_1) 2008; 108 Rohren (ref_3) 2004; 231 Goud (ref_7) 2021; 64 (ref_35) 2012; 55 Miller (ref_6) 2008; 47 Shen (ref_54) 2019; 55 ref_49 Ishii (ref_23) 2012; 3 |
| References_xml | – volume: 8 start-page: 4843 year: 2006 ident: ref_26 article-title: Convenient Method for the Preparation of Weinreb Amides via Pd-Catalyzed Aminocarbonylation of Aryl Bromides at Atmospheric Pressure publication-title: Org. Lett. doi: 10.1021/ol061902t – volume: 21 start-page: 8689 year: 2021 ident: ref_53 article-title: One-Pot Synthesis of 11C-Labelled Primary Benzamides via Intermediate [11C]Aroyl Dimethylaminopyridinium Salts publication-title: Chem. Eur. J. doi: 10.1002/chem.202100544 – volume: 68 start-page: 1233 year: 2011 ident: ref_55 article-title: A phase I study of tasisulam sodium (LY573636 sodium), a novel anticancer compound in patients with refractory solid tumors publication-title: Cancer Chemother. Pharmacol. doi: 10.1007/s00280-011-1593-0 – ident: ref_49 – volume: 4 start-page: 25 year: 2019 ident: ref_14 article-title: [11C]Carbon monoxide: Advances in production and application to PET radiotracer development over the past 15 years publication-title: EJNMMI Radiopharm. Chem. doi: 10.1186/s41181-019-0073-4 – volume: 73 start-page: 7102 year: 2008 ident: ref_27 article-title: Palladium-Catalyzed Carbonylation Reactions of Aryl Bromides at Atmospheric Pressure: A General System Based on Xantphos publication-title: J. Org. Chem. doi: 10.1021/jo801279r – volume: 3 start-page: 804 year: 2012 ident: ref_23 article-title: Synthesis of [11C]Am80 via Novel Pd(0)-Mediated Rapid [11C]Carbonylation Using Arylboronate and [11C]Carbon Monoxide publication-title: ACS Med. Chem. Lett. doi: 10.1021/ml300160w – volume: 64 start-page: 1223 year: 2021 ident: ref_7 article-title: Carbon-11: Radiochemistry and Target-Based PET Molecular Imaging Applications in Oncology, Cardiology, and Neurology publication-title: J. Med. Chem. doi: 10.1021/acs.jmedchem.0c01053 – volume: 61 start-page: 237 year: 2017 ident: ref_11 article-title: Recent progress in [11C]carbon dioxide ([11C]CO2) and [11C]carbon monoxide ([11C]CO) chemistry publication-title: J. Label. Compd. Radiopharm. doi: 10.1002/jlcr.3596 – volume: 17 start-page: 460 year: 2011 ident: ref_29 article-title: Rapid Carbon-11 Radiolabelling for PET Using Microfluidics publication-title: Chem. Eur. J. doi: 10.1002/chem.201002644 – volume: 137 start-page: 1548 year: 2015 ident: ref_38 article-title: Efficient 11C-carbonylation of isolated aryl palladium complexes for PET: Application to challenging radiopharmaceutical synthesis publication-title: J. Am. Chem. Soc. doi: 10.1021/ja511441u – volume: 58 start-page: 65 year: 2015 ident: ref_8 article-title: Development of carbon-11 labelled PET tracers—Radiochemical and technological challenges in a historic perspective publication-title: J. Label. Compd. Radiopharm. doi: 10.1002/jlcr.3258 – volume: 63 start-page: 482 year: 2020 ident: ref_31 article-title: Radiosynthesis of a Bruton’s tyrosine kinase inhibitor, [11C]Tolebrutinib, via palladium-NiXantphos-mediated carbonylation publication-title: J. Label. Compd. Radiopharm. doi: 10.1002/jlcr.3872 – volume: 8 start-page: 26 year: 2018 ident: ref_24 article-title: Featuring Xantphos publication-title: Catal. Sci. Technol. doi: 10.1039/C7CY01629H – volume: 9 start-page: 906 year: 2018 ident: ref_45 article-title: Development of [Carbonyl-11C]AZ13198083, a Novel Histamine Type-3 Receptor Radioligand with Favorable Kinetics publication-title: ACS Chem. Neurosci. doi: 10.1021/acschemneuro.7b00493 – volume: 64 start-page: 9201 year: 1999 ident: ref_18 article-title: Biologically Active 11C-Labeled Amides Using Palladium-Mediated Reactions with Aryl Halides and [11C]Carbon Monoxide publication-title: J. Org. Chem. doi: 10.1021/jo990616a – volume: 45 start-page: 139 year: 2001 ident: ref_2 article-title: Brain radioligands—State of the art and new trends publication-title: J. Nucl. Med. – volume: 48 start-page: 4114 year: 2009 ident: ref_17 article-title: Palladium-catalyzed carbonylation reactions of aryl halides and related compounds publication-title: Angew. Chem. Int. Ed. doi: 10.1002/anie.200900013 – volume: 63 start-page: 517 year: 2020 ident: ref_42 article-title: Development of a fully automated low-pressure [11C]CO carbonylation apparatus publication-title: J. Label. Compd. Radiopharm. doi: 10.1002/jlcr.3866 – volume: 58 start-page: 86 year: 2015 ident: ref_13 article-title: [11C]Carbon monoxide in labeling chemistry and positron emission tomography tracer development: Scope and limitations publication-title: J. Label. Compd. Radiopharm. doi: 10.1002/jlcr.3262 – volume: 108 start-page: 1501 year: 2008 ident: ref_1 article-title: Molecular imaging with PET publication-title: Chem. Rev. doi: 10.1021/cr0782426 – volume: 2013 start-page: 1228 year: 2013 ident: ref_16 article-title: Palladium-mediated [11C]carbonylation at atmospheric pressure: A general method using xantphos as supporting ligand publication-title: Eur. J. Org. Chem. doi: 10.1002/ejoc.201201708 – volume: 351 start-page: 3260 year: 2009 ident: ref_28 article-title: A Microfluidic Approach to the Rapid Screening of Palladium-Catalysed Aminocarbonylation Reactions publication-title: Adv. Synth. Catal. doi: 10.1002/adsc.200900563 – volume: 60 start-page: 504 year: 2019 ident: ref_52 article-title: PET Imaging of PARP Expression Using 18F-Olaparib publication-title: J. Nucl. Med. doi: 10.2967/jnumed.118.213223 – volume: 50 start-page: 794 year: 2007 ident: ref_19 article-title: [11C]carbon monoxide, a versatile and useful precursor in labelling chemistry for PET-ligand development publication-title: J. Label. Compd. Radiopharm. doi: 10.1002/jlcr.1446 – volume: 5 start-page: 8242 year: 2020 ident: ref_43 article-title: Copper(I)-Mediated 11C-Carboxylation of (Hetero)arylstannanes publication-title: ACS Omega doi: 10.1021/acsomega.0c00524 – volume: 1 start-page: 772289 year: 2021 ident: ref_32 article-title: 11C-Radiosynthesis of [11C]Ibrutinib via Pd-Mediated [11C]CO Carbonylation: Preliminary PET Imaging in Experimental Autoimmune Encephalomyelitis Mice publication-title: Front. Nucl. Med. doi: 10.3389/fnume.2021.772289 – volume: 42 start-page: 893 year: 2015 ident: ref_46 article-title: Synthesis of ([11C]carbonyl)raclopride and a comparison with ([11C]methyl)raclopride in a monkey PET study publication-title: Nucl. Med. Biol. doi: 10.1016/j.nucmedbio.2015.07.003 – volume: 61 start-page: 4103 year: 2018 ident: ref_51 article-title: An 18F-Labeled Poly(ADP-ribose) Polymerase Positron Emission Tomography Imaging Agent publication-title: J. Med. Chem. doi: 10.1021/acs.jmedchem.8b00138 – volume: 46 start-page: 1664 year: 2005 ident: ref_4 article-title: PET/CT: Challenge for Nuclear Cardiology publication-title: J. Nucl. Med. – volume: 100 start-page: 2741 year: 2000 ident: ref_25 article-title: Ligand bite angle effects in metal-catalyzed c-c bond formation publication-title: Chem. Rev. doi: 10.1021/cr9902704 – volume: 9 start-page: 12270 year: 2022 ident: ref_5 article-title: PET Molecular Imaging in Drug Development: The Imaging and Chemistry Perspective publication-title: Front. Med. doi: 10.3389/fmed.2022.812270 – volume: 48 start-page: 6001 year: 2009 ident: ref_10 article-title: Methods for the incorporation of carbon-11 to generate radiopharmaceuticals for PET imaging publication-title: Angew. Chem. Int. Ed. doi: 10.1002/anie.200901481 – volume: 231 start-page: 305 year: 2004 ident: ref_3 article-title: Clinical Applications of PET in Oncology publication-title: Radiology doi: 10.1148/radiol.2312021185 – volume: 27 start-page: 1382 year: 2016 ident: ref_37 article-title: Synthesis of Diverse 11C-Labeled PET Radiotracers via Direct Incorporation of [11C]CO2 publication-title: Bioconjug. Chem. doi: 10.1021/acs.bioconjchem.6b00163 – volume: 28 start-page: 2887 year: 2017 ident: ref_57 article-title: Last-Step Pd-Mediated [11C]CO Labeling of a Moxestrol-Conjugated o-Iodobenzyl Alcohol: From Model Experiments to in Vivo Positron Emission Tomography Studies publication-title: Bioconjug. Chem. doi: 10.1021/acs.bioconjchem.7b00583 – volume: 56 start-page: 4549 year: 2017 ident: ref_39 article-title: Application of Methyl Bisphosphine-Ligated Palladium Complexes for Low Pressure N-11C-Acetylation of Peptides publication-title: Angew. Chem. Int. Ed. doi: 10.1002/anie.201700446 – ident: ref_50 – ident: ref_33 – volume: 17 start-page: 354 year: 2015 ident: ref_56 article-title: General Last-Step Labeling of Biomolecule-Based Substrates by [12C], [13C], and [11C]Carbon Monoxide publication-title: Org. Lett. doi: 10.1021/ol503471e – volume: 2007 start-page: 455 year: 2007 ident: ref_34 article-title: Synthesis of [11C]/[13C]Acrylamides by Palladium-Mediated Carbonylation publication-title: Eur. J. Org. Chem. doi: 10.1002/ejoc.200600700 – volume: 92 start-page: 115 year: 2021 ident: ref_15 article-title: The development of 11C-carbonylation chemistry: A systematic view publication-title: Nucl. Med. Biol. doi: 10.1016/j.nucmedbio.2020.02.005 – volume: 55 start-page: 223 year: 2012 ident: ref_22 article-title: Transition metal mediated synthesis using [11C]CO at low pressure—A simplified method for 11C-carbonylation publication-title: J. Label. Compd. Radiopharm. doi: 10.1002/jlcr.2930 – volume: 51 start-page: 11795 year: 2015 ident: ref_48 article-title: [11C]CO2 to [11C]CO conversion mediated by [11C]silanes: A novel route for [11C]carbonylation reactions publication-title: Chem. Commun. doi: 10.1039/C5CC02095F – ident: ref_21 doi: 10.1039/b906166e – volume: 2 start-page: 233 year: 2021 ident: ref_44 article-title: Preclinical Evaluation of TSPO and MAO-B PET Radiotracers in an LPS Model of Neuroinflammation publication-title: PET Clin. doi: 10.1016/j.cpet.2020.12.003 – volume: 47 start-page: 8998 year: 2008 ident: ref_6 article-title: Synthesis of 11C, 18F, 15O, and 13N radiolabels for positron emission tomography publication-title: Angew. Chem. Int. Ed. doi: 10.1002/anie.200800222 – volume: 57 start-page: 195 year: 2014 ident: ref_12 article-title: Transition metal mediated [11C]carbonylation reactions: Recent advances and applications publication-title: J. Label. Compd. Radiopharm. doi: 10.1002/jlcr.3150 – volume: 63 start-page: 100 year: 2020 ident: ref_40 article-title: “In-loop” carbonylation—A simplified method for carbon-11 labelling of drugs and radioligands publication-title: J. Label. Compd. Radiopharm. doi: 10.1002/jlcr.3805 – volume: 12 start-page: 511 year: 2019 ident: ref_47 article-title: Radiolabelling of [11C]FPS-ZM1, a RAGE-targeting PET radiotracer, using a [11C]CO2-to-[11C]CO chemical conversion publication-title: Future Med. Chem. doi: 10.4155/fmc-2019-0329 – volume: 123 start-page: 105 year: 2023 ident: ref_9 article-title: Radiosynthesis, Preclinical, and Clinical Positron Emission Tomography Studies of Carbon-11 Labeled Endogenous and Natural Exogenous Compounds publication-title: Chem. Rev. doi: 10.1021/acs.chemrev.2c00398 – volume: 55 start-page: 3124 year: 2019 ident: ref_54 article-title: Efficient synthesis of carbon-11 labelled acylsulfonamides using [11C]CO carbonylation chemistry publication-title: Chem. Commun. doi: 10.1039/C8CC09661A – volume: 43 start-page: 232 year: 2016 ident: ref_36 article-title: Development of carbon-11 labeled acryl amides for selective PET imaging of active tissue transglutaminase publication-title: Nucl. Med. Biol. doi: 10.1016/j.nucmedbio.2016.01.003 – volume: 1 start-page: 820235 year: 2022 ident: ref_41 article-title: Synthesis of Radiopharmaceuticals via “In-Loop” 11C-Carbonylation as Exemplified by the Radiolabeling of Inhibitors of Bruton’s Tyrosine Kinase publication-title: Front. Nucl. Med. doi: 10.3389/fnume.2021.820235 – volume: 2014 start-page: 304 year: 2013 ident: ref_30 article-title: Improved Yields for the Palladium-Mediated 11C-Carbonylation Reaction Using Microwave Technology publication-title: Eur. J. Org. Chem. – volume: 10 start-page: 558 year: 2004 ident: ref_20 article-title: Utilization of [11C]-labelled boron carbonyl complexes in palladium carbonylation reaction publication-title: Chem. Comm. doi: 10.1039/b314982j – volume: 55 start-page: 477 year: 2012 ident: ref_35 article-title: Combinatorial synthesis of labelled drugs and PET tracers: Synthesis of a focused library of 11C-carbonyl-labelled acrylamides as potential biomarkers of EGFR expression publication-title: J. Label. Compd. Radiopharm. doi: 10.1002/jlcr.2981 |
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| Snippet | The Pd–Xantphos-mediated 11C-carbonylation protocol (also known as the “Xantphos- method”), due to its simplistic and convenient nature, has facilitated... The Pd-Xantphos-mediated 11C-carbonylation protocol (also known as the "Xantphos- method"), due to its simplistic and convenient nature, has facilitated... The Pd–Xantphos-mediated 11 C-carbonylation protocol (also known as the “Xantphos- method”), due to its simplistic and convenient nature, has facilitated... |
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| SubjectTerms | Automation Carbon dioxide Carbon monoxide carbon-11 carbonylation Labeling Ligands Molybdenum radiochemistry radiopharmaceuticals Reagents Review Xantphos |
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| Title | Reactive Palladium–Ligand Complexes for 11C-Carbonylation at Ambient Pressure: A Breakthrough in Carbon-11 Chemistry |
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