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Literature DB >> 27500313

Nucleophilic (Radio)Fluorination of α-Diazocarbonyl Compounds Enabled by Copper-Catalyzed H-F Insertion.

Erin E Gray¹, Matthew K Nielsen¹, Kimberly A Choquette¹, Julia A Kalow¹, Thomas J A Graham², Abigail G Doyle¹.

Abstract

The copper-catalyzed H-F insertion into α-diazocarbonyl compounds is described using potassium fluoride (KF) and hexafluoroisopropanol. Access to complex α-fluorocarbonyl derivatives is achieved under mild conditions, and the method is readily adapted to radiofluorination with [(18)F]KF. This late-stage strategy provides an attractive route to (18)F-labeled biomolecules.

Entities: Chemical

Mesh：

Substances：

Year: 2016 PMID： 27500313 PMCID： PMC9011916 DOI： 10.1021/jacs.6b06770

Source DB: PubMed Journal: J Am Chem Soc ISSN： 0002-7863 Impact factor: 15.419

26 in total

1. Radiosynthesis and evaluation of [18F]Selectfluor bis(triflate).

Authors: Harriet Teare; Edward G Robins; Anna Kirjavainen; Sarita Forsback; Graham Sandford; Olof Solin; Sajinder K Luthra; Véronique Gouverneur
Journal: Angew Chem Int Ed Engl Date: 2010-09-10 Impact factor: 15.336

Review 2. Monofluorination of Organic Compounds: 10 Years of Innovation.

Authors: Pier Alexandre Champagne; Justine Desroches; Jean-Denys Hamel; Mathilde Vandamme; Jean-François Paquin
Journal: Chem Rev Date: 2015-04-09 Impact factor: 60.622

3. Nucleophilic fluorination of β-ketoester derivatives with HBF4.

Authors: Raffaele Pasceri; Hannah E Bartrum; Christopher J Hayes; Christopher J Moody
Journal: Chem Commun (Camb) Date: 2012-11-12 Impact factor: 6.222

4. Late-stage [¹⁸F]Fluorination: New Solutions to Old Problems.

Authors: Allen F Brooks; Joseph J Topczewski; Naoko Ichiishi; Melanie S Sanford; Peter J H Scott
Journal: Chem Sci Date: 2014-12-01 Impact factor: 9.825

5. Nonmetal catalyzed insertion reactions of diazocarbonyls to acid derivatives in fluorinated alcohols.

Authors: Lidia Dumitrescu; Kaouther Azzouzi-Zriba; Danièle Bonnet-Delpon; Benoit Crousse
Journal: Org Lett Date: 2011-01-19 Impact factor: 6.005

6. Enantioselective ring opening of epoxides by fluoride anion promoted by a cooperative dual-catalyst system.

Authors: Julia A Kalow; Abigail G Doyle
Journal: J Am Chem Soc Date: 2010-03-17 Impact factor: 15.419

7. Catalytic X-H insertion reactions based on carbenoids.

Authors: Dennis Gillingham; Na Fei
Journal: Chem Soc Rev Date: 2013-06-21 Impact factor: 54.564

8. A novel aliphatic 18F-labeled probe for PET imaging of melanoma.

Authors: Hongguang Liu; Shuanglong Liu; Zheng Miao; Han Jiang; Zixin Deng; Xuechuan Hong; Zhen Cheng
Journal: Mol Pharm Date: 2013-08-22 Impact factor: 4.939

9. Coordination diversity in hydrogen-bonded homoleptic fluoride-alcohol complexes modulates reactivity.

Authors: Keary M Engle; Lukas Pfeifer; George W Pidgeon; Guy T Giuffredi; Amber L Thompson; Robert S Paton; John M Brown; Véronique Gouverneur
Journal: Chem Sci Date: 2015-06-22 Impact factor: 9.825

Review 10. 18F-Labeled Peptides: The Future Is Bright.

Authors: Susan Richter; Frank Wuest
Journal: Molecules Date: 2014-12-08 Impact factor: 4.411

11 in total

1. (Radio)fluoroclick Reaction Enabled by a Hydrogen-Bonding Cluster.

Authors: Xiaojun Zeng; Junling Li; Chin K Ng; Gerald B Hammond; Bo Xu
Journal: Angew Chem Int Ed Engl Date: 2018-02-13 Impact factor: 15.336

2. Regio- and Stereoselective Synthesis of 1,2-Dihaloalkenes Using In-Situ-Generated ICl, IBr, BrCl, I2, and Br2.

Authors: Xiaojun Zeng; Shiwen Liu; Yuhao Yang; Yi Yang; Gerald B Hammond; Bo Xu
Journal: Chem Date: 2020-04-09 Impact factor: 22.804

3. Synthesis of [¹⁸F]-γ-fluoro-α,β,-unsaturated esters and ketones via vinylogous ¹⁸F-fluorination of α-diazoacetates with [¹⁸F]AgF.

Authors: Stephen Thompson; So Jeong Lee; Isaac M Jackson; Naoko Ichiishi; Allen F Brooks; Melanie S Sanford; Peter J H Scott
Journal: Synthesis (Stuttg) Date: 2019-12 Impact factor: 3.157

Nucleophilic (Radio)Fluorination of α-Diazocarbonyl Compounds Enabled by Copper-Catalyzed H-F Insertion.

1. Radiosynthesis and evaluation of [18F]Selectfluor bis(triflate).

Review 2. Monofluorination of Organic Compounds: 10 Years of Innovation.

3. Nucleophilic fluorination of β-ketoester derivatives with HBF4.

4. Late-stage [¹⁸F]Fluorination: New Solutions to Old Problems.

5. Nonmetal catalyzed insertion reactions of diazocarbonyls to acid derivatives in fluorinated alcohols.

6. Enantioselective ring opening of epoxides by fluoride anion promoted by a cooperative dual-catalyst system.

7. Catalytic X-H insertion reactions based on carbenoids.

8. A novel aliphatic 18F-labeled probe for PET imaging of melanoma.

9. Coordination diversity in hydrogen-bonded homoleptic fluoride-alcohol complexes modulates reactivity.

Review 10. 18F-Labeled Peptides: The Future Is Bright.

1. (Radio)fluoroclick Reaction Enabled by a Hydrogen-Bonding Cluster.

2. Regio- and Stereoselective Synthesis of 1,2-Dihaloalkenes Using In-Situ-Generated ICl, IBr, BrCl, I2, and Br2.

3. Synthesis of [¹⁸F]-γ-fluoro-α,β,-unsaturated esters and ketones via vinylogous ¹⁸F-fluorination of α-diazoacetates with [¹⁸F]AgF.

Review 4. Fluorine-18: Radiochemistry and Target-Specific PET Molecular Probes Design.

5. Enantiospecific Solvolytic Functionalization of Bromochlorides.

6. Copper-Mediated Late-stage Radiofluorination: Five Years of Impact on Pre-clinical and Clinical PET Imaging.

7. Catalytic Asymmetric Fluorination of Copper Carbene Complexes: Preparative Advances and a Mechanistic Rationale.

Review 8. Uncommon carbene insertion reactions.

9. Photoinduced Proton-Transfer Reactions for Mild O-H Functionalization of Unreactive Alcohols.

Review 10. Closing the gap between ¹⁹F and ¹⁸F chemistry.

Review 2. Monofluorination of Organic Compounds: 10 Years of Innovation.

Review 10. 18F-Labeled Peptides: The Future Is Bright.

Review 4. Fluorine-18: Radiochemistry and Target-Specific PET Molecular Probes Design.

Review 8. Uncommon carbene insertion reactions.

Review 10. Closing the gap between 19F and 18F chemistry.

Review 10. Closing the gap between ¹⁹F and ¹⁸F chemistry.