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Literature DB >> 21528150

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

Pazhamalai Anbarasan¹, Thomas Schareina, Matthias Beller.

Abstract

The palladium-catalyzed cyanation of Ar-X (X = I, Br, Cl, OTf, and H) allows for an efficient access towards benzonitriles. After its discovery in 1973 and following significant improvements in recent decades, this methodology has become nowadays the most popular for preparation of substituted aromatic nitriles. In this critical review, we summarize the important developments in this area from 2000 until 2010 (151 references). This journal is © The Royal Society of Chemistry 2011

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Year: 2011 PMID： 21528150 DOI： 10.1039/c1cs15004a

Source DB: PubMed Journal: Chem Soc Rev ISSN： 0306-0012 Impact factor: 54.564

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Cited

34 in total

1. Cyanide-arene Meisenheimer complex generated in electrospray ionization mass spectrometry using acetonitrile as a solvent.

Authors: Barbara Chiavarino; Philippe Maitre; Simonetta Fornarini; Maria Elisa Crestoni
Journal: J Am Soc Mass Spectrom Date: 2013-08-18 Impact factor: 3.109

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. Cobalt-based nanocatalysts for green oxidation and hydrogenation processes.

Authors: Rajenahally V Jagadeesh; Tobias Stemmler; Annette-Enrica Surkus; Matthias Bauer; Marga-Martina Pohl; Jörg Radnik; Kathrin Junge; Henrik Junge; Angelika Brückner; Matthias Beller
Journal: Nat Protoc Date: 2015-05-21 Impact factor: 13.491

4. Delayed catalyst function enables direct enantioselective conversion of nitriles to NH₂-amines.

Authors: Shaochen Zhang; Juan Del Pozo; Filippo Romiti; Yucheng Mu; Sebastian Torker; Amir H Hoveyda
Journal: Science Date: 2019-04-05 Impact factor: 47.728

5. Synthesis of nitriles via palladium-catalyzed water shuffling from amides to acetonitrile.

Authors: Wandi Zhang; Christopher W Haskins; Yang Yang; Mingji Dai
Journal: Org Biomol Chem Date: 2014-12-07 Impact factor: 3.876

6. Mechanistic Insight Facilitates Discovery of a Mild and Efficient Copper-Catalyzed Dehydration of Primary Amides to Nitriles Using Hydrosilanes.

Authors: Richard Y Liu; Minwoo Bae; Stephen L Buchwald
Journal: J Am Chem Soc Date: 2018-01-29 Impact factor: 15.419

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

1. Cyanide-arene Meisenheimer complex generated in electrospray ionization mass spectrometry using acetonitrile as a solvent.

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

3. Cobalt-based nanocatalysts for green oxidation and hydrogenation processes.

4. Delayed catalyst function enables direct enantioselective conversion of nitriles to NH₂-amines.

5. Synthesis of nitriles via palladium-catalyzed water shuffling from amides to acetonitrile.

6. Mechanistic Insight Facilitates Discovery of a Mild and Efficient Copper-Catalyzed Dehydration of Primary Amides to Nitriles Using Hydrosilanes.

7. Off-Cycle Processes in Pd-Catalyzed Cross-Coupling of Carboranes.

8. Synergistic Catalysis: A Powerful Synthetic Strategy for New Reaction Development.

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

10. Rational Development of Remote C-H Functionalization of Biphenyl: Experimental and Computational Studies.