Water as a hydrogen source in palladium-catalyzed reduction and reductive amination of nitroarenes mediated by diboronic acid

Zhou, Yanmei; Zhou, Haifeng; Liu, Sensheng; Pi, Danwei; Shen, Guanshuo

doi:10.1016/j.tet.2017.05.056

Cited by 50 publications

(20 citation statements)

References 46 publications

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“…as the hydrogen source mediated by diboronic acid (B 2 (OH) 4 5 equiv.) in acetonitrile at 80° for 24 h for reacting various nitroarenes with different aromatic and aliphatic aldehydes, affording yields ranging from 60 to 90% ( Scheme 8 ) [ 49 ]. The yields were higher when the substituent in the benzaldehyde ring was electron withdrawing.…”

Section: Metal-catalyzed One-pot Reductive Amination Reactionmentioning

confidence: 99%

Metal-based Heterogeneous Catalysts for One-Pot Synthesis of Secondary Anilines from Nitroarenes and Aldehydes

et al. 2021

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Recently, N-substituted anilines have been the object of increasing research interest in the field of organic chemistry due to their role as key intermediates for the synthesis of important compounds such as polymers, dyes, drugs, agrochemicals and pharmaceutical products. Among the various methods reported in literature for the formation of C–N bonds to access secondary anilines, the one-pot reductive amination of aldehydes with nitroarenes is the most interesting procedure, because it allows to obtain diverse N-substituted aryl amines by simple reduction of nitro compounds followed by condensation with aldehydes and subsequent reduction of the imine intermediates. These kinds of tandem reactions are generally catalyzed by transition metal-based catalysts, mainly potentially reusable metal nanoparticles. The rapid growth in the last years in the field of metal-based heterogeneous catalysts for the one-pot reductive amination of aldehydes with nitroarenes demands for a review on the state of the art with a special emphasis on the different kinds of metals used as catalysts and their recyclability features.

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Section: Metal-catalyzed One-pot Reductive Amination Reactionmentioning

confidence: 99%

Metal-based Heterogeneous Catalysts for One-Pot Synthesis of Secondary Anilines from Nitroarenes and Aldehydes

et al. 2021

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“…Several reports deal with the use of NaBH 4 as a mild, inexpensive, and safe reducing agent in the presence of nickel (Kalbasi and Mazaheri, 2015;Fiore et al, 2019) or palladium nanoparticles (Kalbasi and Mazaheri, 2016). Decaborane (B 10 H 14 ) (Bae et al, 2000) and diboronic acid (B 2 (OH) 4 ) (Zhou Y. et al, 2017) in combination with Pd/C catalyst were also shown to be convenient systems for reductive alkylation of nitroarenes with aromatic and aliphatic aldehydes. Non-catalytic methods utilizing zinc as a reducing agent have also been reported (Zou et al, 2007;Jiang et al, 2009;Wahba and Hamann, 2012;Lin et al, 2016), yet their discussion is beyond the scope of this short review.…”

Section: Intermolecular Reductive Amination Of Aldehydes and Ketones mentioning

confidence: 99%

Catalytic Reductive Amination of Aldehydes and Ketones With Nitro Compounds: New Light on an Old Reaction

Sukhorukov

2020

Front. Chem.

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Reductive amination of carbonyl compounds with primary amines is a well-established synthetic methodology for the selective production of unsymmetrically substituted secondary and tertiary amines. From the industrial and green chemistry perspective, it is attractive to combine reductive amination with the synthesis of primary amines in a single one-pot catalytic process. In this regard, nitro compounds, which are readily available and inexpensive feedstocks, received much attention as convenient precursors to primary amines in such processes. Although the direct reductive coupling of nitro compounds with aldehydes/ketones to give secondary and tertiary amines has been known since the 1940's, due to the development of highly efficient and selective non-noble metal-based catalysts a breakthrough in this area was made in the last decade. In this short overview, recent progress in the methodology of the reductive amination with nitro compounds is summarized together with applications to the synthesis of bioactive amines and heterocycles. Remaining challenges in this field are also analyzed.

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“…[36][37][38][39][40][41][42][43] Potentially attractive aldehydes and ketones can be obtained from the biorefinery processes, [26,44,45] while nitrobenzene is obtained via nitration of benzene. In the transformations of carbonyl compounds with nitroaromatic compounds to secondary amines several monometallic supported catalysts have been applied, such as Pd, [46][47][48] Pt, [30] Au modified by NH 2 groups, [49] Ni supported on H-ZSM-5 zeolite (Ni/H-mZSM-5) [50] and bimetallic noble metal catalysts. [11,51,52] To overcome the high price of noble metal catalysts, cheaper transition metal catalysts have also been applied.…”

Section: Introductionmentioning

confidence: 99%

“…The aim of this review is to elucidate amination of carbonyl compounds from the engineering point of view reporting the effect of the solvent, [14,[23][24][25][26]28,[49][50][51][52]61] reaction conditions, [2,11,14,15,19,23,48,54,61,63,64] catalyst properties, [2,10,11,14,15,17,21,23,24,26,28,30,[46][47][48][50][51][52][59][60][61][65][66][67][68][69] regeneration and reuse, [14,23,25,...…”

Section: Introductionmentioning

confidence: 99%

“…[61] In addition, results on amination of carbonyl compounds in a continuous mode will be discussed in detail. [20,24,63,[71][72][73][74] Another aim is also to understand the catalyst property-performance relationship and elucidate the reaction mechanisms, [2,48,49,54,56,59,63] related to production of secondary amines from carbonyl compounds. Reductive amination of aldehyde/ketone with a primary amine forming in the first step an imine, which is then hydrogenated to an amine, is discussed in Section 2 (Figure 3a), while onepot reductive amination of nitrocompounds with primary amines, which includes as an additional step hydrogenation of the nitro compound to amine, is summarized in Section 3 (Figure 3b).…”

Section: Introductionmentioning

confidence: 99%

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One-pot amination of aldehydes and ketones over heterogeneous catalysts for production of secondary amines

2021

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This review summarizes the recent studies on the synthesis of secondary amines by one-pot amination of aldehydes and ketones over heterogeneous catalysts. Amines are widely applied as the key intermediates in chemical industry for the synthesis of various commodities such as agrochemicals, drugs, detergents, lubricants, food-additives and polymers. Direct catalytic reductive amination of carbonyl compounds was considered which generally includes two steps: (i) formation of imines by interactions of aldehydes or ketones with amines, and (ii) subsequent hydrogenation of imines. Synthesis of secondary amines from carbonyl compounds and amines generated in situ under reaction conditions from their progenitors, e.g., respectively, alcohols or nitro-compounds, is also discussed in detail. Recent progress in application of hydrogen sources alternative to gaseous H 2 , such as formic acid, NaBH 4 , CO and water, favored development of metal-free catalysts including solid acid catalysts. The review addresses the scope of the amination reaction with aldehydes/ketones and nitro/amine compounds of different structure, the effect of the solvent, reaction conditions and catalyst properties. In addition, catalyst regeneration and reuse, kinetic regularities and kinetic modeling with an emphasis on the continuous mode of one-pot amination have been systematically summarized and discussed. It is suggested that the future work should focus on revealing the role of the catalytically active sites addressing their acid-base properties and the correlation between catalyst properties and the reaction performance, elucidating kinetic parameters and designing feasible reactor system for further industrial implementation.

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Water as a hydrogen source in palladium-catalyzed reduction and reductive amination of nitroarenes mediated by diboronic acid

Cited by 50 publications

References 46 publications

Metal-based Heterogeneous Catalysts for One-Pot Synthesis of Secondary Anilines from Nitroarenes and Aldehydes

Metal-based Heterogeneous Catalysts for One-Pot Synthesis of Secondary Anilines from Nitroarenes and Aldehydes

Catalytic Reductive Amination of Aldehydes and Ketones With Nitro Compounds: New Light on an Old Reaction

One-pot amination of aldehydes and ketones over heterogeneous catalysts for production of secondary amines

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