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Literature DB >> 26929068

Synthesis of Aryldifluoroamides by Copper-Catalyzed Cross-Coupling.

Abstract

A copper-catalyzed coupling of aryl, heteroaryl, and vinyl iodides with α-silyldifluoroamides is reported. The reaction forms α,α-difluoro-α-aryl amides from electron-rich, electron-poor, and sterically hindered aryl iodides in high yield and tolerates a variety of functional groups. The aryldifluoroamide products can be transformed further to provide access to a diverse array of difluoroalkylarenes, including compounds of potential biological interest.

Entities: Chemical Disease Gene

Keywords: amides; copper; cross-coupling; fluorine; synthetic methods

Mesh：

Substances：
Amides
Fluorine
Copper

Year: 2016 PMID： 26929068 PMCID： PMC4956475 DOI： 10.1002/anie.201600105

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

18 in total

1. Integration of lead optimization with crystallography for a membrane-bound ion channel target: discovery of a new class of AMPA receptor positive allosteric modulators.

Authors: Simon E Ward; Mark Harries; Laura Aldegheri; Nigel E Austin; Stuart Ballantine; Elisa Ballini; Daniel M Bradley; Benjamin D Bax; Brian P Clarke; Andrew J Harris; Stephen A Harrison; Rosemary A Melarange; Claudette Mookherjee; Julie Mosley; Gianni Dal Negro; Beatrice Oliosi; Kathrine J Smith; Kevin M Thewlis; Patrick M Woollard; Shahnaz P Yusaf
Journal: J Med Chem Date: 2010-12-03 Impact factor: 7.446

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

Authors: Kenichi Fujikawa; Yasutaka Fujioka; Akira Kobayashi; Hideki Amii
Journal: Org Lett Date: 2011-09-28 Impact factor: 6.005

3. Palladium-catalyzed difluoroalkylation of aryl boronic acids: a new method for the synthesis of aryldifluoromethylated phosphonates and carboxylic acid derivatives.

Authors: Zhang Feng; Qiao-Qiao Min; Yu-Lan Xiao; Bo Zhang; Xingang Zhang
Journal: Angew Chem Int Ed Engl Date: 2014-01-22 Impact factor: 15.336

4. Application of the Goldilocks effect to the design of potent and selective inhibitors of phenylethanolamine N-methyltransferase: balancing pKa and steric effects in the optimization of 3-methyl-1,2,3,4-tetrahydroisoquinoline inhibitors by beta-fluorination.

Authors: Gary L Grunewald; Mitchell R Seim; Jian Lu; Mariam Makboul; Kevin R Criscione
Journal: J Med Chem Date: 2006-05-18 Impact factor: 7.446

5. Direct cupration of fluoroform.

Authors: Alessandro Zanardi; Maxim A Novikov; Eddy Martin; Jordi Benet-Buchholz; Vladimir V Grushin
Journal: J Am Chem Soc Date: 2011-12-02 Impact factor: 15.419

6. Nickel-catalyzed cross-coupling of functionalized difluoromethyl bromides and chlorides with aryl boronic acids: a general method for difluoroalkylated arenes.

Authors: Yu-Lan Xiao; Wen-Hao Guo; Guo-Zhen He; Qiang Pan; Xingang Zhang
Journal: Angew Chem Int Ed Engl Date: 2014-07-17 Impact factor: 15.336

7. Cupration of C2F5H: isolation, structure, and synthetic applications of [K(DMF)2][(t-BuO)Cu(C2F5)]. Highly efficient pentafluoroethylation of unactivated aryl bromides.

Authors: Anton Lishchynskyi; Vladimir V Grushin
Journal: J Am Chem Soc Date: 2013-08-19 Impact factor: 15.419

8. Direct synthesis of a trifluoromethyl copper reagent from trifluoromethyl ketones: application to trifluoromethylation.

Authors: Hiroki Serizawa; Kohsuke Aikawa; Koichi Mikami
Journal: Chemistry Date: 2013-11-21 Impact factor: 5.236

Synthesis of Aryldifluoroamides by Copper-Catalyzed Cross-Coupling.

1. Integration of lead optimization with crystallography for a membrane-bound ion channel target: discovery of a new class of AMPA receptor positive allosteric modulators.

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

3. Palladium-catalyzed difluoroalkylation of aryl boronic acids: a new method for the synthesis of aryldifluoromethylated phosphonates and carboxylic acid derivatives.

4. Application of the Goldilocks effect to the design of potent and selective inhibitors of phenylethanolamine N-methyltransferase: balancing pKa and steric effects in the optimization of 3-methyl-1,2,3,4-tetrahydroisoquinoline inhibitors by beta-fluorination.

5. Direct cupration of fluoroform.

6. Nickel-catalyzed cross-coupling of functionalized difluoromethyl bromides and chlorides with aryl boronic acids: a general method for difluoroalkylated arenes.

7. Cupration of C2F5H: isolation, structure, and synthetic applications of [K(DMF)2][(t-BuO)Cu(C2F5)]. Highly efficient pentafluoroethylation of unactivated aryl bromides.

8. Direct synthesis of a trifluoromethyl copper reagent from trifluoromethyl ketones: application to trifluoromethylation.

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

10. Copper-mediated perfluoroalkylation of heteroaryl bromides with (phen)CuRF.

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

2. Synthesis of N-trifluoromethyl amides from carboxylic acids.

3. A practical and catalyst-free trifluoroethylation reaction of amines using trifluoroacetic acid.