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Literature DB >> 20441204

Copper-catalyzed cyanation of heterocycle carbon-hydrogen bonds.

Abstract

A method for regioselective cyanation of heterocycles has been developed. A number of aromatic heterocycles as well as azulene can be cyanated in reasonable to good yields by using a copper cyanide catalyst and an iodine oxidant.

Entities: Chemical Disease

Mesh：

Substances：
Nitriles
Copper
Iodine

Year: 2010 PMID： 20441204 PMCID： PMC2881224 DOI： 10.1021/ol100772u

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

31 in total

Review 1. Practical methodologies for the synthesis of indoles.

Authors: Guy R Humphrey; Jeffrey T Kuethe
Journal: Chem Rev Date: 2006-07 Impact factor: 60.622

Review 2. Aryl-aryl bond formation by transition-metal-catalyzed direct arylation.

Authors: Dino Alberico; Mark E Scott; Mark Lautens
Journal: Chem Rev Date: 2007-01 Impact factor: 60.622

3. Direct cyanation of heteroaromatic compounds mediated by hypervalent iodine(III) reagents: In situ generation of PhI(III)-CN species and their cyano transfer.

Authors: Toshifumi Dohi; Koji Morimoto; Naoko Takenaga; Akihiro Goto; Akinobu Maruyama; Yorito Kiyono; Hirofumi Tohma; Yasuyuki Kita
Journal: J Org Chem Date: 2007-01-05 Impact factor: 4.354

Copper-catalyzed cyanation of heterocycle carbon-hydrogen bonds.

Review 1. Practical methodologies for the synthesis of indoles.

Review 2. Aryl-aryl bond formation by transition-metal-catalyzed direct arylation.

3. Direct cyanation of heteroaromatic compounds mediated by hypervalent iodine(III) reagents: In situ generation of PhI(III)-CN species and their cyano transfer.

Review 4. Comprehensive pharmacology and clinical efficacy of aromatase inhibitors.

Review 5. Escitalopram: a review of its use in the management of major depressive disorder.

6. Copper-catalyzed domino halide exchange-cyanation of aryl bromides.

7. Copper-catalyzed arene C-H bond cross-coupling.

8. Application of Daugulis copper-catalyzed direct arylation to the synthesis of 5-aryl benzotriazepines.

9. An aromatic Glaser-Hay reaction.

Review 10. Palladium(II)-catalyzed C-H activation/C-C cross-coupling reactions: versatility and practicality.

1. A general method for copper-catalyzed arene cross-dimerization.

2. Rapid, Microwave Accelerated Synthesis of [1,2,4]Triazolo[3,4-b][1,3,4]oxadiazoles from 4-Acylamino-1,2,4-Triazoles.

Review 3. Direct cyanation, hydrocyanation, dicyanation and cyanofunctionalization of alkynes.

4. Improved Schmidt Conversion of Aldehydes to Nitriles Using Azidotrimethylsilane in 1,1,1,3,3,3-Hexafluoro-2-propanol.

5. Nucleophilic C-H Etherification of Heteroarenes Enabled by Base-Catalyzed Halogen Transfer.

6. Direct α-heteroarylation of amides (α to nitrogen) and ethers through a benzaldehyde-mediated photoredox reaction.