Cobalt(II)‐Catalyzed <i>N</i>‐Acylation of Amines through a Transamidation Reaction

Ma, Jian‐Ping; Zhang, Feng; Zhang, Jingyu; Gong, Hang

doi:10.1002/ejoc.201800253

Cited by 18 publications

(10 citation statements)

References 78 publications

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“…Based on the previous literature report (Ma and Gong, 2018) and our results, a reasonable reaction mechanism has been proposed (Scheme 1). Initially, the carbonyl group of chitin is activated by Cu(OAc) 2 catalyst through coordination.…”

Section: Resultssupporting

confidence: 63%

Selective Utilization of N-acetyl Groups in Chitin for Transamidation of Amines

Shen

Liu

et al. 2021

Front. Chem. Eng.

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The selective transformation of chitin into various renewable N-containing chemicals and medicines has attracted increasing attention. However, the N-acetyl groups in chitin construct strong hydrogen bond networks, which restricts its depolymerization and transformation. The selective conversion of robust chitin commonly requires considerable base catalysts to remove the N-acetyl group as a byproduct in advance, which is non-compliance with the principle of atomic economy. Herein, for the first time we demonstrate a novel approach to achieve the selective utilization of the N-acetyl group in chitin for transamidation of chitin with amines. A series of amine derivatives, mainly including aliphatic amine, cyclic amine and functionalized aromatic amine, could be selectively converted into the corresponding amide products frequently found in pharmaceuticals. Furthermore, the solid residue after removing the acetyl group (denoted as De-chitin) with the sufficient exposure of -NH2 groups as a solid base catalyst shows excellent performance in the aldol condensation reaction of furfural and acetone to produce fuel precursors. Our process provides a strategy that exploiting every functional group adequately in substrates to obtain value-added chemicals.

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Section: Resultssupporting

confidence: 63%

Selective Utilization of N-acetyl Groups in Chitin for Transamidation of Amines

Shen

Liu

et al. 2021

Front. Chem. Eng.

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“…Nucleophilic addition of R 1 R 2 NH to the latter followed by elimination of 1,2,4-triazole and Cu II affords the product [107]. Such a pathway contrasts with the proposal of Gong and co-workers who assumed the direct amine addition to the DMF/Co II complex [109] as above alleged under Fe III catalysis [92]. No mechanism was indicated by L. Zhang's team for the Pd-catalyzed reaction [108]; the yield decreased in the absence of NEt 3 (Scheme 33j), leading us to suspect a pathway similar to that mediated by Cu II .…”

Section: Rc=o Fragmentmentioning

confidence: 63%

“…Heating was required for the amidation of arylamines mediated with graphene oxide under neat conditions (Scheme 34f) [106]. N-Amidation of aryl and aliphatic amines arose in high yields at 80-150 °C under CuCl2 (Scheme 33i) [107] or PdCl2 catalysis (Scheme 33j) [108] while Co(OAc)2 as catalyst was efficient only from aliphatic amines (Scheme 33k) [109]. The Cu-catalyzed reaction was carried out in the presence of 1,2,4-triazole.…”

Section: Rc=o Fragmentmentioning

confidence: 99%

A Journey from June 2018 to October 2021 with N,N-Dimethylformamide and N,N-Dimethylacetamide as Reactants

Мuzart¹

2021

Molecules

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“…Mesoporous niobium oxide spheres [ 37 ] and N -heterocyclic carbene ruthenium (II) complexes [ 38 ] are some of the most general and easy to use catalysts with the best substrate scope. Very recently, the use of Co(AcO) 2 ⋅4H 2 O was described [ 39 ] with an excellent substrate scope, but there are no special considerations to mention here.…”

Section: Metal-catalyzed Direct Transamidationsmentioning

confidence: 99%

Direct Transamidation Reactions: Mechanism and Recent Advances

2018

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Amides are undeniably some of the most important compounds in Nature and the chemical industry, being present in biomolecules, materials, pharmaceuticals and many other substances. Unfortunately, the traditional synthesis of amides suffers from some important drawbacks, principally the use of stoichiometric activators or the need to use highly reactive carboxylic acid derivatives. In recent years, the transamidation reaction has emerged as a valuable alternative to prepare amides. The reactivity of amides makes their direct reaction with nitrogen nucleophiles difficult; thus, the direct transamidation reaction needs a catalyst in order to activate the amide moiety and to promote the completion of the reaction because equilibrium is established. In this review, we present research on direct transamidation reactions ranging from studies of the mechanism to the recent developments of more applicable and versatile methodologies, emphasizing those reactions involving activation with metal catalysts.

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Cobalt(II)‐Catalyzed N‐Acylation of Amines through a Transamidation Reaction

Cited by 18 publications

References 78 publications

Selective Utilization of N-acetyl Groups in Chitin for Transamidation of Amines

Selective Utilization of N-acetyl Groups in Chitin for Transamidation of Amines

A Journey from June 2018 to October 2021 with N,N-Dimethylformamide and N,N-Dimethylacetamide as Reactants

Direct Transamidation Reactions: Mechanism and Recent Advances

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