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Literature DB >> 28834065

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

Maruthi Kumar Narayanam¹, Gaoyuan Ma¹, Pier Alexandre Champagne², Kendall N Houk², Jennifer M Murphy¹.

Abstract

A practical method for radiofluorination of anilines with [18 F]fluoride via N-arylsydnone intermediates is described. These precursors are stable, easy to handle and facilitate direct and regioselective 18 F-labeling to prepare [18 F]fluoroarenes. The value of this methodology is further highlighted by successful application to prepare an 18 F-labeled neuropeptide.

Entities: Chemical Disease Gene

Keywords: click chemistry; fluorine-18; fluoroarene; peptide radiolabeling; sydnone

Mesh：

Substances：

Year: 2017 PMID： 28834065 PMCID： PMC5674999 DOI： 10.1002/anie.201707274

Source DB: PubMed Journal: Angew Chem Int Ed Engl ISSN： 1433-7851 Impact factor: 15.336

56 in total

1. The activation strain model of chemical reactivity.

Authors: Willem-Jan van Zeist; F Matthias Bickelhaupt
Journal: Org Biomol Chem Date: 2010-05-20 Impact factor: 3.876

2. Distortion/interaction energy control of 1,3-dipolar cycloaddition reactivity.

Authors: Daniel H Ess; K N Houk
Journal: J Am Chem Soc Date: 2007-08-09 Impact factor: 15.419

3. Protective effect of delta opioid receptor agonist (D-Ala2, D-Leu5) enkephalin on permanent focal cerebral ischemia in rats.

Authors: Danyun Fu; Haitong Liu; Hui Zhu; Shitong Li; Junyan Yao
Journal: Neuroreport Date: 2016-07-06 Impact factor: 1.837

4. Copper(I)-catalyzed cycloaddition of 4-bromosydnones and alkynes for the regioselective synthesis of 1,4,5-trisubstituted pyrazoles.

Authors: Elodie Decuypere; Simon Specklin; Sandra Gabillet; Davide Audisio; Hui Liu; Lucie Plougastel; Sergii Kolodych; Frédéric Taran
Journal: Org Lett Date: 2014-12-29 Impact factor: 6.005

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

Authors: Joong-Hyun Chun; Cheryl L Morse; Frederick T Chin; Victor W Pike
Journal: Chem Commun (Camb) Date: 2013-02-07 Impact factor: 6.222

6. Copper-mediated fluorination of arylboronate esters. Identification of a copper(III) fluoride complex.

Authors: Patrick S Fier; Jingwei Luo; John F Hartwig
Journal: J Am Chem Soc Date: 2013-02-05 Impact factor: 15.419

7. 4-Halogeno-sydnones for fast strain promoted cycloaddition with bicyclo-[6.1.0]-nonyne.

Authors: Lucie Plougastel; Oleksandr Koniev; Simon Specklin; Elodie Decuypere; Christophe Créminon; David-Alexandre Buisson; Alain Wagner; Sergii Kolodych; Frédéric Taran
Journal: Chem Commun (Camb) Date: 2014-08-25 Impact factor: 6.222

8. Diels-Alder Reactivities of Benzene, Pyridine, and Di-, Tri-, and Tetrazines: The Roles of Geometrical Distortions and Orbital Interactions.

Authors: Yun-Fang Yang; Yong Liang; Fang Liu; K N Houk
Journal: J Am Chem Soc Date: 2016-02-02 Impact factor: 15.419

9. Formation of ArF from LPdAr(F): catalytic conversion of aryl triflates to aryl fluorides.

Authors: Donald A Watson; Mingjuan Su; Georgiy Teverovskiy; Yong Zhang; Jorge García-Fortanet; Tom Kinzel; Stephen L Buchwald
Journal: Science Date: 2009-08-13 Impact factor: 47.728

10. Copper-Mediated Radiofluorination of Arylstannanes with [¹⁸F]KF.

Authors: Katarina J Makaravage; Allen F Brooks; Andrew V Mossine; Melanie S Sanford; Peter J H Scott
Journal: Org Lett Date: 2016-10-10 Impact factor: 6.005

6 in total

1. Direct arene C-H fluorination with ¹⁸F^- via organic photoredox catalysis.

Authors: Wei Chen; Zeng Huang; Nicholas E S Tay; Benjamin Giglio; Mengzhe Wang; Hui Wang; Zhanhong Wu; David A Nicewicz; Zibo Li
Journal: Science Date: 2019-06-21 Impact factor: 47.728

Review 2. 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

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

1. The activation strain model of chemical reactivity.

2. Distortion/interaction energy control of 1,3-dipolar cycloaddition reactivity.

3. Protective effect of delta opioid receptor agonist (D-Ala2, D-Leu5) enkephalin on permanent focal cerebral ischemia in rats.

4. Copper(I)-catalyzed cycloaddition of 4-bromosydnones and alkynes for the regioselective synthesis of 1,4,5-trisubstituted pyrazoles.

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

6. Copper-mediated fluorination of arylboronate esters. Identification of a copper(III) fluoride complex.

7. 4-Halogeno-sydnones for fast strain promoted cycloaddition with bicyclo-[6.1.0]-nonyne.

8. Diels-Alder Reactivities of Benzene, Pyridine, and Di-, Tri-, and Tetrazines: The Roles of Geometrical Distortions and Orbital Interactions.

9. Formation of ArF from LPdAr(F): catalytic conversion of aryl triflates to aryl fluorides.

10. Copper-Mediated Radiofluorination of Arylstannanes with [¹⁸F]KF.

1. Direct arene C-H fluorination with ¹⁸F^- via organic photoredox catalysis.

Review 2. Chemistry for Positron Emission Tomography: Recent Advances in ¹¹ C-, ¹⁸ F-, ¹³ N-, and ¹⁵ O-Labeling Reactions.

3. Origins of halogen effects in bioorthogonal sydnone cycloadditions.

4. A General Protocol for Cu-Mediated Fluoro-deamination: Sandmeyer Fluorination of Diverse Aromatic Substrates.

Review 5. Recent Advances in Synthetic Methodologies to Form C-¹⁸F Bonds.

Review 6. Closing the gap between ¹⁹F and ¹⁸F chemistry.

Review 2. Chemistry for Positron Emission Tomography: Recent Advances in 11 C-, 18 F-, 13 N-, and 15 O-Labeling Reactions.

Review 5. Recent Advances in Synthetic Methodologies to Form C-18F Bonds.

Review 6. Closing the gap between 19F and 18F chemistry.

Review 2. Chemistry for Positron Emission Tomography: Recent Advances in ¹¹ C-, ¹⁸ F-, ¹³ N-, and ¹⁵ O-Labeling Reactions.

Review 5. Recent Advances in Synthetic Methodologies to Form C-¹⁸F Bonds.

Review 6. Closing the gap between ¹⁹F and ¹⁸F chemistry.