Laboratory-Scale Synthesis of Nitriles by Catalysed Dehydration of Amides and Oximes under Flash Vacuum Pyrolysis (FVP) Conditions

Campbell, Jacqueline A.; McDougald, Graham; McNab, Hamish; Rees, Lovat V.C.; Tyas, Richard G.

doi:10.1055/s-2007-990782

Synthesis

2007

DOI: 10.1055/s-2007-990782

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Laboratory-Scale Synthesis of Nitriles by Catalysed Dehydration of Amides and Oximes under Flash Vacuum Pyrolysis (FVP) Conditions

Jacqueline A. Campbell¹,

Graham McDougald²,

Hamish McNab³

et al.

Abstract: Dehydration of amides and oximes can be catalysed by 3 Å molecular sieves or by tungsten trioxide under flash vacuum pyrolysis (FVP) conditions. This provides a convenient synthesis of aliphatic, aromatic, and heterocyclic nitriles, generally in excellent yields under mild, neutral, and short contact time conditions.

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Cited by 12 publications

References 8 publications

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Metal‐Catalyzed Dehydration of Primary Amides to Nitriles

Al‐Huniti

Croatt

2019

Asian J Org Chem

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The dehydration of primary amides to generate their respective nitriles is an isohypsic, or redox neutral, method to install a valuable functional group into a molecule. This process has been known for over 175 years, typically using highly reactive dehydrating agents and high temperatures. Recently, transition metal-catalysis has enabled reactivity under milder reaction conditions, while also tolerating a wide range of functional groups. The removal of water from primary amides is still energetically uphill so a stoichiometric dehydrating agent is required. The dehydrating agents used in recent years can be rather benign, such as acetonitrile to generate acetamide. This Minireview focuses on metalcatalyzed reactions to convert primary amides into nitriles and is organized based on the dehydrating agent.[a] Dr. Figure 1. Bioactive compounds containing a nitrile. Scheme 1. Methods for dehydration of amides. 2 3 4 5 6 7 8

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Metal‐Catalyzed Dehydration of Primary Amides to Nitriles

Al‐Huniti

Croatt

2019

Asian J Org Chem

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Copper-Catalyzed Dehydration of Primary Amides to Nitriles

Enthaler

Weidauer

2011

Catal Lett

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In the present study we introduce a coppercatalyzed protocol for the dehydration of primary amides to their corresponding nitriles applying N-methyl-N-(trimethylsilyl)trifluoroacetamide (MSTFA) as silylation reagent. For that purpose investigations of various reaction parameters (copper source, solvent, temperature, MSTFA and copper loading) have been carried out to find suitable reaction conditions. Simple copper(I) chloride (2.5 mol%) and MSTFA (2.0 equiv) in toluene allow for the straightforward synthesis of a variety of nitriles (15 examples).

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Acidic hierarchical porous ZSM-5 assembled palladium catalyst: A green substitute to transform primary amides to nitriles

Chen

Zhang

et al. 2022

Applied Catalysis B: Environmental

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Laboratory-Scale Synthesis of Nitriles by Catalysed Dehydration of Amides and Oximes under Flash Vacuum Pyrolysis (FVP) Conditions

Cited by 12 publications

References 8 publications

Metal‐Catalyzed Dehydration of Primary Amides to Nitriles

Metal‐Catalyzed Dehydration of Primary Amides to Nitriles

Copper-Catalyzed Dehydration of Primary Amides to Nitriles

Acidic hierarchical porous ZSM-5 assembled palladium catalyst: A green substitute to transform primary amides to nitriles

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