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Literature DB >> 19422207

A general and convenient catalytic synthesis of nitriles from amides and silanes.

Shaolin Zhou¹, Kathrin Junge, Daniele Addis, Shoubhik Das, Matthias Beller.

Abstract

A new and convenient protocol for the catalytic dehydration of aromatic and aliphatic amides using silanes in the presence of catalytic amounts of fluoride is presented. The synthesis of aliphatic and aromatic nitriles proceeds with high selectivity under mild conditions. Notably, a wide substrate range is converted in good to excellent yields.

Entities: Chemical Disease

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Year: 2009 PMID： 19422207 DOI： 10.1021/ol900716q

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

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Cited

9 in total

1. 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

2. 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

A general and convenient catalytic synthesis of nitriles from amides and silanes.

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

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

3. 2,2',6,6'-Tetra-ethyl-4,4'-methyl-enedibenzonitrile.

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

5. Catalytic Promiscuity of Galactose Oxidase: A Mild Synthesis of Nitriles from Alcohols, Air, and Ammonia.

6. A Cyanide-Free Synthesis of Acylcyanides through Ru-Catalyzed C(sp³)-H-Oxidation of Benzylic Nitriles.

7. One pot synthesis of aryl nitriles from aromatic aldehydes in a water environment.

8. Preparation of Polyfunctionalized Aromatic Nitriles from Aryl Oxazolines.

9. Development and Utilization of a Palladium-Catalyzed Dehydration of Primary Amides To Form Nitriles.