Synthesis of Nitriles from Primary Amides or Aldoximes under Conditions of a Catalytic Swern Oxidation

Ding, Rui; Liu, Yongguo; Han, Mengru; Jiao, Wenyi; Li, Jiaqi; Tian, Hongyu; Sun, Baoguo

doi:10.1021/acs.joc.8b02190

Cited by 73 publications

(41 citation statements)

References 38 publications

(43 reference statements)

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“…In addition, researchers have found that primary amides or aldoximes can be dehydrated to give nitriles 103 under Swern oxidation conditions (Scheme ) …”

Section: Dehydrationmentioning

confidence: 99%

Oxalyl Chloride: A Versatile Reagent in Organic Transformations

Mohammadkhani

Heravi

2019

ChemistrySelect

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Oxalyl chloride, (COCl)2, as an inexpensive commercially available chemical is one of the most versatile applicable organic reagents in chemical transformations. It is also employed extensively in various chemical industries. It is employed in various chemical transformations such as chlorination, oxidation, reduction, dehydration, decarboxylation, and formylation reactions as well as ring cleavage of epoxides. During the past decades, numerous procedures using (COCl)2 as reagent have been developed and published. However, its importance has largely been overlooked by the absence of a comprehensive review in chemical literature dealing with its application in organic transformations and its utilization in the chemical industry. This Review aims to provide an overview for the applications of oxalyl chloride in organic synthesis, including its physical properties, synthesis, as well as its unique roles as the reagent in organic reactions, covering the literature over the past 103 years (from 1916 to date).

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“…In addition, researchers have found that primary amides or aldoximes can be dehydrated to give nitriles 103 under Swern oxidation conditions (Scheme ) …”

Section: Dehydrationmentioning

confidence: 99%

Oxalyl Chloride: A Versatile Reagent in Organic Transformations

Mohammadkhani

Heravi

2019

ChemistrySelect

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“…To date, various methods for the synthesis of nitriles have been developed using different starting substrates, reagents and reaction conditions (Scheme ). Nitriles have been prepared from amines ( I ), amides ( II ), aldehydes ( III ), oximes ( IV ), amidoximes ( V ), thioamides ( VI ), alkyl‐halides/azides ( VII ), nitroalkanes ( VIII ), anilines/arylhalides ( IX ), and alcohols ( X ) . On larger scale, nitriles are commonly produced via the ammoxidation or hydrocyanation methods .…”

Section: Introductionmentioning

confidence: 99%

Methods of Nitriles Synthesis from Amines through Oxidative Dehydrogenation

Patil

Gupta

2020

Adv Synth Catal

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In recent years, oxidative dehydrogenation (ODH) of amines has proven to be an efficient, clean and fundamental route for the synthesis of nitriles. This review focuses on the different types of reactions for the oxidation of amines to nitriles such as transition metal-catalysis, photoactivation, acceptorless dehydrogenation, nitroxyl radical-mediated, and N,O-doped mesoporous carbon. Emphasis is placed on the ODH of amines to the corresponding nitriles using ruthenium catalysts. Metal free systems utilizing iodine, TEMPO and its derivatives, TCCA with or without additives are also discussed. The ODH of amines using N,O-doped mesoporous carbon is elaborated. Attention is also given to major improvements, achievements, and challenges that still remain in the field of nitrile synthesis from amines. 2.3. Photocatalytic System 2.4. Acceptorless Dehydrogenation (AD) 2.5. Substrate Scope and Functional Group Tolerance 3.

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“…[1][2][3][4][5][6] Oximes serve as key synthons for the preparation of carbonyl amines, nitriles, amides, thiohydroxamic and thiohydroxic acid derivatives, nitro compounds, and oxime esters. [7][8][9][10][11][12][13][14] For example, cyclohexanone oxime is widely used in industry as a key intermediate for the synthesis of caprolactam, which is the precursor of Nylon 6. 15 Oximes have also drawn considerable attention in supramolecular chemistry due to their ability to both accept and donate hydrogen bonds and thus their capacity to form dimers and catemers.…”

Section: Introductionmentioning

confidence: 99%

OxymaPure Coupling Reagents: Beyond Solid-Phase Peptide Synthesis

et al. 2020

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OxymaPure [ethyl 2-cyano-2-(hydroxyimino)acetate] is an exceptional reagent with which to suppress racemization and enhance coupling efficiency during amide bond formation. The tremendous popularity of OxymaPure has led to the development of several Oxyma-based reagents. OxymaPure and its derived reagents are widely used in solid- and solution-phase peptide chemistry. This review summarizes the recent developments and applications of OxymaPure and Oxyma-based reagents in peptide chemistry, in particular in solution-phase chemistry. Moreover, the side reaction associated with OxymaPure is also discussed.1 Introduction2 Oxyma-Based Coupling Reagents2.1 Aminium/Uronium Salts of OxymaPure2.2 Phosphonium Salts of OxymaPure2.3 Oxyma-Based Phosphates2.4 Sulfonate Esters of OxymaPure2.5 Benzoate Esters of OxymaPure2.6 Carbonates of OxymaPure Derivatives3 OxymaPure Derivatives4 Other Oxime-Based Additives and Coupling Reagents5 Side Reactions Using OxymaPure Derivatives6 Conclusion7 List of Abbreviations

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Synthesis of Nitriles from Primary Amides or Aldoximes under Conditions of a Catalytic Swern Oxidation

Cited by 73 publications

References 38 publications

Oxalyl Chloride: A Versatile Reagent in Organic Transformations

Oxalyl Chloride: A Versatile Reagent in Organic Transformations

Methods of Nitriles Synthesis from Amines through Oxidative Dehydrogenation

OxymaPure Coupling Reagents: Beyond Solid-Phase Peptide Synthesis

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