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Publication

Nickel-Catalyzed Reductive Transamidation of Secondary Amides with Nitroarenes

Xile Hu, Chi Wai Cheung, Marten Leendert Ploeger
2017
Journal Articles

Abstract

Transmidation is an attractive method for amide synthesis. However, transamidation of secondary amides is challenging. Here, we describe a reductive transamidation method that employs readily available nitro(hetero)arenes as the nitrogen sources, zinc or manganese as reductant, and simple nickel salt and ligand as a catalyst system. The scope of amides includes both alkyl and aryl secondary amides, with high functional group compatibility.

Official source

https://infoscience.epfl.ch/entities/publication/097a398f-624b-42cf-9190-a0cf6035a065

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Xile Hu, Chi Wai Cheung, Marten Leendert Ploeger
2017
Journal Articles

Abstract

Official source

https://infoscience.epfl.ch/entities/publication/097a398f-624b-42cf-9190-a0cf6035a065

About this result

Related concepts (9)

Amide

In organic chemistry, an amide, also known as an organic amide or a carboxamide, is a compound with the general formula , where R, R', and R′′ represent any group, typically organyl groups or hydrogen atoms. The amide group is called a peptide bond when it is part of the main chain of a protein, and an isopeptide bond when it occurs in a side chain, such as in the amino acids asparagine and glutamine. It can be viewed as a derivative of a carboxylic acid () with the hydroxyl group () replaced by an amine group (); or, equivalently, an acyl (alkanoyl) group () joined to an amine group.

Amine

In chemistry, amines (əˈmi:n,_ˈæmi:n, ˈeɪmiːn) are compounds and functional groups that contain a basic nitrogen atom with a lone pair. Amines are formally derivatives of ammonia (), wherein one or more hydrogen atoms have been replaced by a substituent such as an alkyl or aryl group (these may respectively be called alkylamines and arylamines; amines in which both types of substituent are attached to one nitrogen atom may be called alkylarylamines). Important amines include amino acids, biogenic amines, trimethylamine, and aniline.

Secondary (chemistry)

Secondary is a term used in organic chemistry to classify various types of compounds (e. g. alcohols, alkyl halides, amines) or reactive intermediates (e. g. alkyl radicals, carbocations). An atom is considered secondary if it has two 'R' Groups attached to it. An 'R' group is a carbon containing group such as a methyl (CH3 ). A secondary compound is most often classified on an alpha carbon (middle carbon) or a nitrogen. The word secondary comes from the root word 'second' which means two.

Related publications (7)

Nickel-Catalyzed Reductive Transamidation of Secondary Amides with Nitroarenes

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