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Literature DB >> 23616443

Manganese-catalyzed oxidative benzylic C-H fluorination by fluoride ions.

Abstract

An efficient protocol for the selective fluorination of benzylic C-H bonds is described. The process is catalyzed by manganese salen complexes and uses nucleophilic fluorine sources, such as triethylamine trihydrofluoride and KF. Reaction rates are sufficiently high (30 min) to allow adoption for the incorporation of (18)F fluoride sources for PET imaging applications.

Entities: Chemical

Mesh：

Substances：
Manganese
Fluorides

Year: 2013 PMID： 23616443 DOI： 10.1002/anie.201301097

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

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Cited

22 in total

1. Oxidative aliphatic C-H fluorination with manganese catalysts and fluoride ion.

Authors: Wei Liu; Xiongyi Huang; John T Groves
Journal: Nat Protoc Date: 2013-10-31 Impact factor: 13.491

2. Ligand-Enabled Stereoselective β-C(sp(3))-H Fluorination: Synthesis of Unnatural Enantiopure anti-β-Fluoro-α-amino Acids.

Authors: Ru-Yi Zhu; Keita Tanaka; Gen-Cheng Li; Jian He; Hai-Yan Fu; Su-Hua Li; Jin-Quan Yu
Journal: J Am Chem Soc Date: 2015-05-27 Impact factor: 15.419

3. A Visible-Light-Mediated Radical Smiles Rearrangement and its Application to the Synthesis of a Difluoro-Substituted Spirocyclic ORL-1 Antagonist.

Authors: James J Douglas; Haley Albright; Martin J Sevrin; Kevin P Cole; Corey R J Stephenson
Journal: Angew Chem Int Ed Engl Date: 2015-10-16 Impact factor: 15.336

10. Visible light-promoted metal-free C-H activation: diarylketone-catalyzed selective benzylic mono- and difluorination.

Authors: Ji-Bao Xia; Chen Zhu; Chuo Chen
Journal: J Am Chem Soc Date: 2013-11-12 Impact factor: 15.419

Manganese-catalyzed oxidative benzylic C-H fluorination by fluoride ions.

1. Oxidative aliphatic C-H fluorination with manganese catalysts and fluoride ion.

2. Ligand-Enabled Stereoselective β-C(sp(3))-H Fluorination: Synthesis of Unnatural Enantiopure anti-β-Fluoro-α-amino Acids.

3. A Visible-Light-Mediated Radical Smiles Rearrangement and its Application to the Synthesis of a Difluoro-Substituted Spirocyclic ORL-1 Antagonist.

4. Visible light-promoted metal-free sp(3)-C-H fluorination.

Review 5. Oxygen Activation and Radical Transformations in Heme Proteins and Metalloporphyrins.

6. Decarboxylative Fluorination of Aliphatic Carboxylic Acids via Photoredox Catalysis.

7. Vanadium-Catalyzed C(sp³)-H Fluorination Reactions.

8. Silver-catalyzed vinylogous fluorination of vinyl diazoacetates.

9. Mechanism of Electrophilic Fluorination with Pd(IV): Fluoride Capture and Subsequent Oxidative Fluoride Transfer^.

10. Visible light-promoted metal-free C-H activation: diarylketone-catalyzed selective benzylic mono- and difluorination.