Catalytic Transfer Reductive Cleavage of azo Compounds to Amines Using Chitosan-supported Formate and Zinc

Han, Yuqi; Yu, Xia; Xu, Letian; Song, Hai; Yan, G. F.; Ma, Xiaochen; Zhen, Yuan

doi:10.3184/174751912x13553360452222

Cited by 4 publications

(1 citation statement)

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“…It is extremely important to develop aniline products and their derivatives, especially fine chemical products, to enlarge the market capacity of aniline and improve the economic benefit of enterprises. In recent years, heterogeneous and biocatalytic conversion of the azo compound to amines has been reported. − However, most of these reactions are characterized by harsh conditions and low yields, which makes it necessary to develop simple, rapid, effective, and sustainable alternatives to hydrogenation of the azo compound to amines.…”

Section: Introductionmentioning

confidence: 99%

Theoretical Study on the Mechanism of the Hydrogenation of Azo (N═N) Bonds to Amines Catalyzed by Manganese

Huo,

Xie,

Zhang

et al. 2023

J. Phys. Chem. A

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Section: Introductionmentioning

confidence: 99%

Theoretical Study on the Mechanism of the Hydrogenation of Azo (N═N) Bonds to Amines Catalyzed by Manganese

Huo,

Xie,

Zhang

et al. 2023

J. Phys. Chem. A

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Manganese Catalyzed Hydrogenation of Azo (N=N) Bonds to Amines

et al. 2021

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We report the first example of homogeneously catalyzed hydrogenation of the N=N bond of azo compounds using a complex of an earth‐abundant‐metal. The hydrogenation reaction is catalyzed by a manganese pincer complex, proceeds under mild conditions, and yields amines, which makes this methodology a sustainable alternative route for the conversion of azo compounds. A plausible mechanism involving metal‐ligand cooperation and hydrazine intermediacy is proposed based on mechanistic studies.

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A Mild and Chemoselective Reduction of Nitro and Azo Compounds Catalyzed by a Well‐Defined Mo₃S₄ Cluster Bearing Diamine Ligands

et al. 2015

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Herein, we report a novel well‐defined diamino Mo3S4‐based catalyst system for the reduction of nitroarenes and azo compounds to the corresponding anilines with silanes as reducing agents. This catalytic protocol provides a facile route to access aromatic amines under mild conditions in good to excellent yields. Notably, even anilines functionalized with other potentially reducible moieties are obtained with high selectivity. The new chemoselective catalyst of formula [Mo3S4Cl3(dmen)3](BF4) (dmen: N,N′‐dimethylethylenediamine) is conveniently synthesized through coordination of the diamine ligand to the incomplete Mo3S4 cubane‐type cluster core in a one‐pot two‐step procedure. The crystal structure of the [Mo3S4Cl3(dmen)3]+ cation confirms the formation of a single isomer in which the chlorine atom lies trans to the bridging sulfur atom to afford a C3 symmetry complex with intrinsic backbone chirality. The structure is preserved in solution, as evidenced by multinuclear NMR spectroscopy and electrospray‐ionization mass spectrometric techniques.

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Catalytic Transfer Reductive Cleavage of azo Compounds to Amines Using Chitosan-supported Formate and Zinc

Abstract: A convenient method for the cleavage of azo derivatives to the corresponding amines using chitosan-supported formate as hydrogen donors in conjunction with zinc is described.

Cited by 4 publications

References 22 publications

Theoretical Study on the Mechanism of the Hydrogenation of Azo (N═N) Bonds to Amines Catalyzed by Manganese

Theoretical Study on the Mechanism of the Hydrogenation of Azo (N═N) Bonds to Amines Catalyzed by Manganese

Manganese Catalyzed Hydrogenation of Azo (N=N) Bonds to Amines

A Mild and Chemoselective Reduction of Nitro and Azo Compounds Catalyzed by a Well‐Defined Mo₃S₄ Cluster Bearing Diamine Ligands

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Catalytic Transfer Reductive Cleavage of azo Compounds to Amines Using Chitosan-supported Formate and Zinc

Abstract: A convenient method for the cleavage of azo derivatives to the corresponding amines using chitosan-supported formate as hydrogen donors in conjunction with zinc is described.

Cited by 4 publications

References 22 publications

Theoretical Study on the Mechanism of the Hydrogenation of Azo (N═N) Bonds to Amines Catalyzed by Manganese

Theoretical Study on the Mechanism of the Hydrogenation of Azo (N═N) Bonds to Amines Catalyzed by Manganese

Manganese Catalyzed Hydrogenation of Azo (N=N) Bonds to Amines

A Mild and Chemoselective Reduction of Nitro and Azo Compounds Catalyzed by a Well‐Defined Mo3S4 Cluster Bearing Diamine Ligands

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Product

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A Mild and Chemoselective Reduction of Nitro and Azo Compounds Catalyzed by a Well‐Defined Mo₃S₄ Cluster Bearing Diamine Ligands