K<sub>2</sub>CO<sub>3</sub>-promoted synthesis of amides from 1-aryl-2,2,2-trifluoroethanones and amines under mild conditions

Zhong, Pinyong; Wang, Yu-Chao; Liu, Jin-Biao; Zhang, Linjun; Luo, Nianhua

doi:10.1039/d3ra03329e

Cited by 4 publications

(1 citation statement)

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“…Among the nonconventional approaches, several protocols for the construction of amides have also been established via C–C bond cleavage using glyoxalic acids, ketones, 2,2,2-trifluoroethyl carbonyls, etc. (Scheme B) . Strategies for the formation of amides via C–C bond cleavage generally require metal catalysts, specific amines, and oxidants.…”

Section: Introductionmentioning

confidence: 99%

Sulfur-Mediated Decarboxylative Amidation of Cinnamic Acids via C═C Bond Cleavage

Kumar,

Sharma,

Ishu

et al. 2024

J. Org. Chem.

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Section: Introductionmentioning

confidence: 99%

Sulfur-Mediated Decarboxylative Amidation of Cinnamic Acids via C═C Bond Cleavage

Kumar,

Sharma,

Ishu

et al. 2024

J. Org. Chem.

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Molecular Oxygen‐Induced Transamidation of Unactivated Amides in Diethyl Carbonate in the Presence of a Palladium Catalyst

Urgoitia,

Obieta,

Herrero

et al. 2023

Adv Synth Catal

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Herein we disclose a palladium‐catalyzed procedure for the transamidation of structurally diverse amides with amines based on the use of molecular oxygen as palladium‐activating agent. The reaction, which is scalable and amenable for the preparation of enantioenriched compounds, is carried out in a bio‐degradable solvent often used as a fuel additive, diethyl carbonate. As a result of 10‐4 mol% of catalyst required, final products are isolated containing palladium impurities in a concentration of 0.1 ppm. Two kinetically different mechanistic pathways are proposed for this reaction on account of a number of experiments such as kinetic curves, TEM images, catalyst poisoning experiments, UPLC‐ESI‐MS identification of intermediates and EPR spectra of reaction crude.

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Visible‐Light‐Driven Method for the Selective Synthesis of Amides and N‐Acylureas from Carboxylic Acids and Thioureas

Zhong,

Yang,

Liu

et al. 2024

Chemistry A European J

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In this work, we developed a visible‐light‐driven method for the selective synthesis of amides and N‐acylureas from carboxylic acids and thioureas. This protocol was featured as avoidance of additional oxidants and transition metal catalysts, simple manipulations, low cost, broad substrate scope, and good functional group tolerance. As only oxygen serves as the oxidation reagent, this method provides a promising synthesis candidate for the formation of N‐aryl amides and N‐acylureas, including late‐stage functionalization of complex pharmaceutical molecules and biologically active molecules.

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K₂CO₃-promoted synthesis of amides from 1-aryl-2,2,2-trifluoroethanones and amines under mild conditions

Abstract: A base-promoted amidation of 1-aryl-2,2,2-trifluoroethanones with amines via Haller–Bauer reaction has been developed. This reaction directly transforms aryl trifluoroethanone into amides without the use of stoichiometric chemical oxidants or transition-metal catalysts.

Cited by 4 publications

References 62 publications

Sulfur-Mediated Decarboxylative Amidation of Cinnamic Acids via C═C Bond Cleavage

Sulfur-Mediated Decarboxylative Amidation of Cinnamic Acids via C═C Bond Cleavage

Molecular Oxygen‐Induced Transamidation of Unactivated Amides in Diethyl Carbonate in the Presence of a Palladium Catalyst

Visible‐Light‐Driven Method for the Selective Synthesis of Amides and N‐Acylureas from Carboxylic Acids and Thioureas

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K2CO3-promoted synthesis of amides from 1-aryl-2,2,2-trifluoroethanones and amines under mild conditions

Abstract: A base-promoted amidation of 1-aryl-2,2,2-trifluoroethanones with amines via Haller–Bauer reaction has been developed. This reaction directly transforms aryl trifluoroethanone into amides without the use of stoichiometric chemical oxidants or transition-metal catalysts.

Cited by 4 publications

References 62 publications

Sulfur-Mediated Decarboxylative Amidation of Cinnamic Acids via C═C Bond Cleavage

Sulfur-Mediated Decarboxylative Amidation of Cinnamic Acids via C═C Bond Cleavage

Molecular Oxygen‐Induced Transamidation of Unactivated Amides in Diethyl Carbonate in the Presence of a Palladium Catalyst

Visible‐Light‐Driven Method for the Selective Synthesis of Amides and N‐Acylureas from Carboxylic Acids and Thioureas

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K₂CO₃-promoted synthesis of amides from 1-aryl-2,2,2-trifluoroethanones and amines under mild conditions