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Literature DB >> 21955064

A new method for aromatic difluoromethylation: copper-catalyzed cross-coupling and decarboxylation sequence from aryl iodides.

Kenichi Fujikawa¹, Yasutaka Fujioka, Akira Kobayashi, Hideki Amii.

Abstract

A new methodology for aromatic difluoromethylation is described. Aryl iodides reacted with α-silyldifluoroacetates upon treatment with copper catalyst in DMSO or DME to give the corresponding aryldifluoroacetates in moderate to good yields. The subsequent hydrolysis of aryldifluoroacetates and KF-promoted decarboxylation afforded a variety of difluoromethyl aromatics.

Entities: Chemical

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Year: 2011 PMID： 21955064 DOI： 10.1021/ol202289z

Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.005

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Cited

23 in total

1. Synthesis of Aryldifluoroamides by Copper-Catalyzed Cross-Coupling.

Authors: Sophie I Arlow; John F Hartwig
Journal: Angew Chem Int Ed Engl Date: 2016-03-01 Impact factor: 15.336

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

A new method for aromatic difluoromethylation: copper-catalyzed cross-coupling and decarboxylation sequence from aryl iodides.

1. Synthesis of Aryldifluoroamides by Copper-Catalyzed Cross-Coupling.

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

3. Copper-mediated difluoromethylation of aryl and vinyl iodides.

4. Chlorodifluoromethane-triggered formation of difluoromethylated arenes catalysed by palladium.

5. A new reagent for direct difluoromethylation.

6. Palladium-catalyzed intramolecular C-H difluoroalkylation: synthesis of substituted 3,3-difluoro-2-oxindoles.

7. Palladium-Catalyzed Aryldifluoromethylation of Aryl Halides with Aryldifluoromethyl Trimethylsilanes.

8. Photochemical C-F Activation Enables Defluorinative Alkylation of Trifluoroacetates and -Acetamides.

9. Difluoroalkylation of Tertiary Amides and Lactams by an Iridium-Catalyzed Reductive Reformatsky Reaction.

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