Catalyst-free amidation of aldehyde with amine under mild conditions

Yang, Hongyin; Hu, Wenjian; Deng, Shengjue; Wu, Tiantian; Cen, Haiman; Zhang, Dela; Wang, Bo

doi:10.1039/c5nj01372k

Cited by 19 publications

(8 citation statements)

References 65 publications

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“…In 2015, Wang's research team revealed a catalyst‐free one‐pot procedure for synthesising amide derivatives from amidation reaction of various aromatic and aliphatic aldehydes with 1° and 2° amines trichloroisocyanuric acid in either organic or aqueous media under mild conditions (Scheme 156). [297] …”

Section: C−h Bond Amidationmentioning

confidence: 99%

Cross‐Coupling of C−H and N−H Bonds: A Hydrogen Evolution Strategy for the Construction of C−N Bonds

et al. 2022

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The progress in CÀ N bond construction is significant in synthetic and biological chemistry. Cross-dehydrogenative couplings of CÀ H and NÀ H motifs serve as a unique class of the most atom-economical and straightforward strategies for constructing CÀ N bonds. Herein, we enclosed the most updated methodologies developed in the assembly of CÀ N bonds via photo-catalyzed, transition-metal-catalyzed, electrochemical, and metal-free amination and amidation reactions of saturated and unsaturated CÀ H bonds. Compared with the well-established transition-metal-catalyzed protocols, electricity, or visible light-mediated amination and amidation reactions are competent and appealing. Plausible mechanistic pathways are also described in representative amidation and amination reactions to provide insights for the future development of environmentally kind processes.

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Section: C−h Bond Amidationmentioning

confidence: 99%

Cross‐Coupling of C−H and N−H Bonds: A Hydrogen Evolution Strategy for the Construction of C−N Bonds

et al. 2022

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“…Further development of this methodology was carried out by Wang and co‐workers to obtain amides from aldehydes and amines using TCCA as an oxidizing and chlorinating reagent (Scheme ) …”

Section: Tcca As Oxidizing Reagentmentioning

confidence: 99%

Trichloroisocyanuric Acid: a Versatile and Efficient Chlorinating and Oxidizing Reagent

et al. 2019

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Trichloroisocyanuric acid (TCCA) is a versatile and efficient reagent for chlorination and oxidation reactions. Depending on the reaction conditions employed, it can release either an electrophile chlorine atom (Cl+) or a radical chlorine atom (Cl.) promoting selectively different pathways of reaction. It was effectively used to synthesize many classes of compounds such as: chlorinated arenes, N‐chloramines and amides, α‐halo‐carbonyl compounds, benzyl chlorides, esters, carboxylic anhydrides, and amides. The procedures, which make use of TCCA, have mild reaction conditions and optimal stoichiometric molar ratio of reactants and avoid the use of any metal‐based catalysts. In all cases very high yield and selectivity were observed. The easy and safe handling, the stability, and the low cost of this reagent make it particularly attractive for large‐scale use and industrial applications.

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“…In 2015, Yang et al. described an efficient catalyst‐free procedure for the direct amidation of aldehydes with primary and secondary amines by using TCCA (Scheme ) . This reaction worked smoothly and efficiently in both aqueous solutions and organic solvents.…”

Section: Synthesis Of Amides From Aldehydesmentioning

confidence: 99%

Carbonyl Compounds′ Journey to Amide Bond Formation

Reddy

Beatriz

Lima

2019

Chemistry An Asian Journal

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The formation of amide bonds is one of the most stimulating emerging areas in organic and medicinal chemistry.A mides are recognized as central building blocks in a plethora of interesting pharmaceuticals, proteins, peptides, polymers, naturalp roducts, functional materials, andb iologically relevant carbocyclic or heterocyclic molecules, and they are also found in av ariety of industrial fields. Therefore, a review of recent developments and challenges in the formation of amide bonds from carbonyl compounds is particular-ly important. Herein, we have scrutinized ar ange of metalcatalyzed andm etal-free approaches for the synthesis of amides from aldehydes, ketones, and oximes. In addition, this Minireview highlightsr elevant mechanistic studies, as well as the potential applications of these methods in the synthesis of candidate drug molecules. We hope that the data compiled herein will encourage further progress in this notable area of chemistry research.

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Catalyst-free amidation of aldehyde with amine under mild conditions

Cited by 19 publications

References 65 publications

Cross‐Coupling of C−H and N−H Bonds: A Hydrogen Evolution Strategy for the Construction of C−N Bonds

Cross‐Coupling of C−H and N−H Bonds: A Hydrogen Evolution Strategy for the Construction of C−N Bonds

Trichloroisocyanuric Acid: a Versatile and Efficient Chlorinating and Oxidizing Reagent

Carbonyl Compounds′ Journey to Amide Bond Formation

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