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Literature DB >> 23388835

No-carrier-added [18F]fluoroarenes from the radiofluorination of diaryl sulfoxides.

Joong-Hyun Chun¹, Cheryl L Morse, Frederick T Chin, Victor W Pike.

Abstract

No-carrier-added [(18)F]fluoroarenes were synthesized through the radiofluorination of diaryl sulfoxides with [(18)F]fluoride ion. Diaryl sulfoxides bearing a para electron-withdrawing substituent readily gave the corresponding 4-[(18)F]fluoroarenes in high RCYs. This process broadens the scope for preparing novel (18)F-labeling synthons and PET radiotracers.

Entities: Chemical Gene

Mesh：

Substances：

Year: 2013 PMID： 23388835 PMCID： PMC3587981 DOI： 10.1039/c3cc37795d

Source DB: PubMed Journal: Chem Commun (Camb) ISSN： 1359-7345 Impact factor: 6.222

9 in total

1. Rapid and Efficient Radiosyntheses of Meta-substituted [F]Fluoroarenes from [F]Fluoride Ion and Diaryliodonium Tosylates within a Microreactor.

Authors: Joong-Hyun Chun; Shuiyu Lu; Victor W Pike
Journal: European J Org Chem Date: 2011-08

2. Selective syntheses of no-carrier-added 2- and 3-[18F]fluorohalopyridines through the radiofluorination of halopyridinyl(4'-methoxyphenyl)iodonium tosylates.

Authors: Joong-Hyun Chun; Victor W Pike
Journal: Chem Commun (Camb) Date: 2012-08-30 Impact factor: 6.222

3. In vivo binding to peripheral benzodiazepine binding sites in lesioned rat brain: comparison between [3H]PK11195 and [18F]PK14105 as markers for neuronal damage.

Authors: G W Price; R G Ahier; S P Hume; R Myers; L Manjil; J E Cremer; S K Luthra; C Pascali; V Pike; R S Frackowiak
Journal: J Neurochem Date: 1990-07 Impact factor: 5.372

Review 4. Fluorine-18-labelled fluoropyridines: advances in radiopharmaceutical design.

Authors: F Dollé
Journal: Curr Pharm Des Date: 2005 Impact factor: 3.116

5. Fast and high-yield microreactor syntheses of ortho-substituted [(18)F]fluoroarenes from reactions of [(18)F]fluoride ion with diaryliodonium salts.

Authors: Joong-Hyun Chun; Shuiyu Lu; Yong-Sok Lee; Victor W Pike
Journal: J Org Chem Date: 2010-05-21 Impact factor: 4.354

6. NCA 16 alpha-[18F]fluoroestradiol-17 beta: the effect of reaction vessel on fluorine-18 resolubilization, product yield, and effective specific activity.

Authors: J W Brodack; M R Kilbourn; M J Welch; J A Katzenellenbogen
Journal: Int J Rad Appl Instrum A Date: 1986

7. Positron emission tomography provides molecular imaging of biological processes.

Authors: M E Phelps
Journal: Proc Natl Acad Sci U S A Date: 2000-08-01 Impact factor: 11.205

8. The radiosynthesis of [18F]PK 14105 as an alternative radioligand for peripheral type benzodiazepine binding sites.

Authors: C Pascali; S K Luthra; V W Pike; G W Price; R G Ahier; S P Hume; R Myers; L Manjil; J E Cremer
Journal: Int J Rad Appl Instrum A Date: 1990

9. Nucleophilic 18F-fluorination of heteroaromatic iodonium salts with no-carrier-added [18F]fluoride.

Authors: Tobias L Ross; Johannes Ermert; Carsten Hocke; Heinz H Coenen
Journal: J Am Chem Soc Date: 2007-05-31 Impact factor: 15.419

9 in total

11 in total

1. Synthesis of [¹⁸ F]Fluoroarenes by Nucleophilic Radiofluorination of N-Arylsydnones.

Authors: Maruthi Kumar Narayanam; Gaoyuan Ma; Pier Alexandre Champagne; Kendall N Houk; Jennifer M Murphy
Journal: Angew Chem Int Ed Engl Date: 2017-09-07 Impact factor: 15.336

2. Quinuclidine and DABCO Enhance the Radiofluorinations of 5-Substituted 2-Halopyridines.

Authors: Gregory R Naumiec; Lisheng Cai; Shuiyu Lu; Victor W Pike
Journal: European J Org Chem Date: 2017-09-04

Review 3. Chemistry for Positron Emission Tomography: Recent Advances in ¹¹ C-, ¹⁸ F-, ¹³ N-, and ¹⁵ O-Labeling Reactions.

Authors: Xiaoyun Deng; Jian Rong; Lu Wang; Neil Vasdev; Lei Zhang; Lee Josephson; Steven H Liang
Journal: Angew Chem Int Ed Engl Date: 2019-01-14 Impact factor: 15.336

4. Total Radiosynthesis: Thinking outside "the box".

Authors: Steven H Liang; Neil Vasdev
Journal: Aust J Chem Date: 2015-08-28 Impact factor: 1.321

5. Single-step syntheses of no-carrier-added functionalized [18F]fluoroarenes as labeling synthons from diaryliodonium salts.

Authors: Joong-Hyun Chun; Victor W Pike
Journal: Org Biomol Chem Date: 2013-10-07 Impact factor: 3.876

10. A concise method for fully automated radiosyntheses of [¹⁸F]JNJ-46356479 and [¹⁸F]FITM via Cu-mediated ¹⁸F-fluorination of organoboranes.

Authors: Gengyang Yuan; Timothy M Shoup; Sung-Hyun Moon; Anna-Liisa Brownell
Journal: RSC Adv Date: 2020-07-02 Impact factor: 4.036

No-carrier-added [18F]fluoroarenes from the radiofluorination of diaryl sulfoxides.

1. Rapid and Efficient Radiosyntheses of Meta-substituted [F]Fluoroarenes from [F]Fluoride Ion and Diaryliodonium Tosylates within a Microreactor.

2. Selective syntheses of no-carrier-added 2- and 3-[18F]fluorohalopyridines through the radiofluorination of halopyridinyl(4'-methoxyphenyl)iodonium tosylates.

3. In vivo binding to peripheral benzodiazepine binding sites in lesioned rat brain: comparison between [3H]PK11195 and [18F]PK14105 as markers for neuronal damage.

Review 4. Fluorine-18-labelled fluoropyridines: advances in radiopharmaceutical design.

5. Fast and high-yield microreactor syntheses of ortho-substituted [(18)F]fluoroarenes from reactions of [(18)F]fluoride ion with diaryliodonium salts.

6. NCA 16 alpha-[18F]fluoroestradiol-17 beta: the effect of reaction vessel on fluorine-18 resolubilization, product yield, and effective specific activity.

7. Positron emission tomography provides molecular imaging of biological processes.

8. The radiosynthesis of [18F]PK 14105 as an alternative radioligand for peripheral type benzodiazepine binding sites.

9. Nucleophilic 18F-fluorination of heteroaromatic iodonium salts with no-carrier-added [18F]fluoride.

1. Synthesis of [¹⁸ F]Fluoroarenes by Nucleophilic Radiofluorination of N-Arylsydnones.

2. Quinuclidine and DABCO Enhance the Radiofluorinations of 5-Substituted 2-Halopyridines.

Review 3. Chemistry for Positron Emission Tomography: Recent Advances in ¹¹ C-, ¹⁸ F-, ¹³ N-, and ¹⁵ O-Labeling Reactions.

4. Total Radiosynthesis: Thinking outside "the box".

5. Single-step syntheses of no-carrier-added functionalized [18F]fluoroarenes as labeling synthons from diaryliodonium salts.

6. Synthesis of meta-substituted [(18)F]3-fluoro-4-aminopyridine via direct radiofluorination of pyridine N-oxides.

7. Sequential Ir/Cu-Mediated Method for the Meta-Selective C-H Radiofluorination of (Hetero)Arenes.

8. Sulfonium salts as leaving groups for aromatic labelling of drug-like small molecules with fluorine-18.

Review 9. 18F-labelled intermediates for radiosynthesis by modular build-up reactions: newer developments.

10. A concise method for fully automated radiosyntheses of [¹⁸F]JNJ-46356479 and [¹⁸F]FITM via Cu-mediated ¹⁸F-fluorination of organoboranes.

Review 4. Fluorine-18-labelled fluoropyridines: advances in radiopharmaceutical design.

Review 3. Chemistry for Positron Emission Tomography: Recent Advances in 11 C-, 18 F-, 13 N-, and 15 O-Labeling Reactions.

Review 9. 18F-labelled intermediates for radiosynthesis by modular build-up reactions: newer developments.

Review 3. Chemistry for Positron Emission Tomography: Recent Advances in ¹¹ C-, ¹⁸ F-, ¹³ N-, and ¹⁵ O-Labeling Reactions.