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Literature DB >> 24760777

Silver-catalyzed oxidative activation of benzylic C-H bonds for the synthesis of difluoromethylated arenes.

Peng Xu¹, Shuo Guo, Liyan Wang, Pingping Tang.

Abstract

A mild and catalytic method to form difluoromethylated arenes through the activation of benzylic C-H bonds has been developed. Utilizing AgNO3 as the catalyst, various arenes with diverse functional groups undergo activation/fluorination of benzylic C-H bonds with commercially available Selectfluor reagent as a source of fluorine in aqueous solution. The reaction is operationally simple and amenable to gram-scale synthesis.

Entities: Chemical

Keywords: CH activation; arenes; fluorination; silver; synthetic methods

Mesh：

Substances：
Fluorine
Silver

Year: 2014 PMID： 24760777 DOI： 10.1002/anie.201400225

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

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Cited

21 in total

1. Ketone-catalyzed photochemical C(sp³)-H chlorination.

Authors: Lei Han; Jibao Xia; Lin You; Chuo Chen
Journal: Tetrahedron Date: 2017-05-04 Impact factor: 2.457

2. 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

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

Authors: Ji-Bao Xia; Chen Zhu; Chuo Chen
Journal: Chem Commun (Camb) Date: 2014-10-11 Impact factor: 6.222

4. Metal-free ¹⁸F-labeling of aryl-CF₂H via nucleophilic radiofluorination and oxidative C-H activation.

Authors: Gengyang Yuan; Feng Wang; Nickeisha A Stephenson; Lu Wang; Benjamin H Rotstein; Neil Vasdev; Pingping Tang; Steven H Liang
Journal: Chem Commun (Camb) Date: 2016-12-20 Impact factor: 6.222

5. Radical C(sp3)-H functionalization and cross-coupling reactions.

Authors: Dung L Golden; Sung-Eun Suh; Shannon S Stahl
Journal: Nat Rev Chem Date: 2022-05-17 Impact factor: 34.571

6. Copper-Catalyzed Functionalization of Benzylic C-H Bonds with N-Fluorobenzenesulfonimide: Switch from C-N to C-F Bond Formation Promoted by a Redox Buffer and Brønsted Base.

Authors: Joshua A Buss; Aristidis Vasilopoulos; Dung L Golden; Shannon S Stahl
Journal: Org Lett Date: 2020-07-29 Impact factor: 6.005

Silver-catalyzed oxidative activation of benzylic C-H bonds for the synthesis of difluoromethylated arenes.

1. Ketone-catalyzed photochemical C(sp³)-H chlorination.

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

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

4. Metal-free ¹⁸F-labeling of aryl-CF₂H via nucleophilic radiofluorination and oxidative C-H activation.

5. Radical C(sp3)-H functionalization and cross-coupling reactions.

6. Copper-Catalyzed Functionalization of Benzylic C-H Bonds with N-Fluorobenzenesulfonimide: Switch from C-N to C-F Bond Formation Promoted by a Redox Buffer and Brønsted Base.

7. N-Directed fluorination of unactivated Csp³-H bonds.

8. Mild silver-mediated geminal difluorination of styrenes using an air- and moisture-stable fluoroiodane reagent.

9. Pd-catalyzed α-arylation of trimethylsilyl enolates of α,α-difluoroacetamides.

10. Arylation of gem-difluoroalkenes using a Pd/Cu Co-catalytic system that avoids β-fluoride elimination.