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Literature DB >> 23934947

A general, practical palladium-catalyzed cyanation of (hetero)aryl chlorides and bromides.

Todd D Senecal¹, Wei Shu, Stephen L Buchwald.

Abstract

Playing it safe: The nontoxic cyanide source K4 [Fe(CN)6]·3H2O can be used for the cyanation of (hetero)aryl halides. The application of palladacycle catalysts prevents poisoning during catalyst formation, thereby allowing for low catalyst loadings, fast reaction times, and wide heterocyclic substrate scope.

Entities: Chemical Disease Gene

Keywords: cross-coupling; cyanides; heterocycles; homogeneous catalysis; palladium

Mesh：

Substances：

Year: 2013 PMID： 23934947 PMCID： PMC3845028 DOI： 10.1002/anie.201304188

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

21 in total

1. Catalytic C-C, C-N, and C-O Ullmann-type coupling reactions.

Authors: Florian Monnier; Marc Taillefer
Journal: Angew Chem Int Ed Engl Date: 2009 Impact factor: 15.336

Review 2. Large-scale applications of transition metal-catalyzed couplings for the synthesis of pharmaceuticals.

Authors: Javier Magano; Joshua R Dunetz
Journal: Chem Rev Date: 2011-03-09 Impact factor: 60.622

3. Highly N2-selective palladium-catalyzed arylation of 1,2,3-triazoles.

Authors: Satoshi Ueda; Mingjuan Su; Stephen L Buchwald
Journal: Angew Chem Int Ed Engl Date: 2011-08-18 Impact factor: 15.336

4. A practical synthesis of 2-((1H-pyrrolo[2,3-b]pyridine-4-yl)methylamino)-5- fluoronicotinic acid.

Authors: Xin Wang; Ben Zhi; Jean Baum; Ying Chen; Richard Crockett; Liang Huang; Shawn Eisenberg; John Ng; Robert Larsen; Mike Martinelli; Paul Reider
Journal: J Org Chem Date: 2006-05-12 Impact factor: 4.354

5. Ligand-free palladium-catalyzed cyanation of aryl halides.

Authors: Steven A Weissman; Daniel Zewge; Cheng Chen
Journal: J Org Chem Date: 2005-02-18 Impact factor: 4.354

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

Authors: Jacopo Zanon; Artis Klapars; Stephen L Buchwald
Journal: J Am Chem Soc Date: 2003-03-12 Impact factor: 15.419

Review 7. Recent developments and perspectives in palladium-catalyzed cyanation of aryl halides: synthesis of benzonitriles.

Authors: Pazhamalai Anbarasan; Thomas Schareina; Matthias Beller
Journal: Chem Soc Rev Date: 2011-04-28 Impact factor: 54.564

8. Mechanisms of catalyst poisoning in palladium-catalyzed cyanation of haloarenes. remarkably facile C-N bond activation in the [(Ph3P)4Pd]/[Bu4N]+ CN- system.

Authors: Stefan Erhardt; Vladimir V Grushin; Alison H Kilpatrick; Stuart A Macgregor; William J Marshall; D Christopher Roe
Journal: J Am Chem Soc Date: 2008-03-13 Impact factor: 15.419

9. Novel trans-spanned palladium complexes as efficient catalysts in mild and amine-free cyanation of aryl bromides under air.

Authors: Olga Grossman; Dmitri Gelman
Journal: Org Lett Date: 2006-03-16 Impact factor: 6.005

10. Completely N1-selective palladium-catalyzed arylation of unsymmetric imidazoles: application to the synthesis of nilotinib.

Authors: Satoshi Ueda; Mingjuan Su; Stephen L Buchwald
Journal: J Am Chem Soc Date: 2011-12-14 Impact factor: 15.419

12 in total

1. Hydrophilic, Potent, and Selective 7-Substituted 2-Aminoquinolines as Improved Human Neuronal Nitric Oxide Synthase Inhibitors.

Authors: Anthony V Pensa; Maris A Cinelli; Huiying Li; Georges Chreifi; Paramita Mukherjee; Linda J Roman; Pavel Martásek; Thomas L Poulos; Richard B Silverman
Journal: J Med Chem Date: 2017-08-04 Impact factor: 7.446

2. Virtually instantaneous, room-temperature [(11)C]-cyanation using biaryl phosphine Pd(0) complexes.

Authors: Hong Geun Lee; Phillip J Milner; Michael S Placzek; Stephen L Buchwald; Jacob M Hooker
Journal: J Am Chem Soc Date: 2015-01-09 Impact factor: 15.419

3. Nitrile in the Hole: Discovery of a Small Auxiliary Pocket in Neuronal Nitric Oxide Synthase Leading to the Development of Potent and Selective 2-Aminoquinoline Inhibitors.

Authors: Maris A Cinelli; Huiying Li; Georges Chreifi; Thomas L Poulos; Richard B Silverman
Journal: J Med Chem Date: 2017-04-19 Impact factor: 7.446

A general, practical palladium-catalyzed cyanation of (hetero)aryl chlorides and bromides.

1. Catalytic C-C, C-N, and C-O Ullmann-type coupling reactions.

Review 2. Large-scale applications of transition metal-catalyzed couplings for the synthesis of pharmaceuticals.

3. Highly N2-selective palladium-catalyzed arylation of 1,2,3-triazoles.

4. A practical synthesis of 2-((1H-pyrrolo[2,3-b]pyridine-4-yl)methylamino)-5- fluoronicotinic acid.

5. Ligand-free palladium-catalyzed cyanation of aryl halides.

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

Review 7. Recent developments and perspectives in palladium-catalyzed cyanation of aryl halides: synthesis of benzonitriles.

8. Mechanisms of catalyst poisoning in palladium-catalyzed cyanation of haloarenes. remarkably facile C-N bond activation in the [(Ph3P)4Pd]/[Bu4N]+ CN- system.

9. Novel trans-spanned palladium complexes as efficient catalysts in mild and amine-free cyanation of aryl bromides under air.

10. Completely N1-selective palladium-catalyzed arylation of unsymmetric imidazoles: application to the synthesis of nilotinib.

1. Hydrophilic, Potent, and Selective 7-Substituted 2-Aminoquinolines as Improved Human Neuronal Nitric Oxide Synthase Inhibitors.

2. Virtually instantaneous, room-temperature [(11)C]-cyanation using biaryl phosphine Pd(0) complexes.

3. Nitrile in the Hole: Discovery of a Small Auxiliary Pocket in Neuronal Nitric Oxide Synthase Leading to the Development of Potent and Selective 2-Aminoquinoline Inhibitors.

4. Well-defined nickel and palladium precatalysts for cross-coupling.

5. Palladium-Catalyzed Enantioselective Redox-Relay Heck Alkynylation of Alkenols To Access Propargylic Stereocenters.

6. Mild palladium-catalyzed cyanation of (hetero)aryl halides and triflates in aqueous media.

Review 7. Recent advances and prospects in the palladium-catalyzed cyanation of aryl halides.

8. An optimized procedure for direct access to 1H-indazole-3-carboxaldehyde derivatives by nitrosation of indoles.

9. N-substituted 2-aminobiphenylpalladium methanesulfonate precatalysts and their use in C-C and C-N cross-couplings.

10. Regioselective synthesis of benzimidazolones via cascade C-N coupling of monosubstituted ureas.