A Highly Active Nano-Palladium Catalyst for the Preparation of Aromatic Azos under Mild Conditions

Hu, Lei; Cao, Xueqing; Shi, Leilei; Qi, Fenqiang; Guo, Zhiqiang; Lu, Jianmei; Gu, Hongwei

doi:10.1021/ol202362f

Cited by 87 publications

(33 citation statements)

References 37 publications

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“…Furthermore, the recovered Au/Mg 4 Al HT can also be reused at least four times without an appreciable loss of activity on this scale, for which the total turnover number (TON) approached 92 000 (Scheme S3) 16. Compared to the palladium‐12a,c and platinum‐based12b nanorods which require inorganic bases (such as KOH) to catalyze the hydrogenative coupling of nitroarenes, Au/Mg 4 Al HT has a TON which is at least two orders of magnitude greater than that of the reported catalysts under additive‐free reaction conditions. Transmission electron microscopy (TEM), X‐ray photoelectron spectroscopy (XPS), and X‐ray diffraction (XRD) confirmed almost no change in the dispersion of the gold or metallic state of gold before and after reuse.…”

Section: Hydrogenative Coupling Of Nitrobenzene To Azobenzene Over Aumentioning

confidence: 90%

Gold‐Catalyzed Direct Hydrogenative Coupling of Nitroarenes To Synthesize Aromatic Azo Compounds

Liu

et al. 2014

Angewandte Chemie

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The azo linkage is a prominent chemical motif which has found numerous applications in materials science, pharmaceuticals, and agrochemicals. Described herein is a sustainable heterogeneous‐gold‐catalyzed synthesis of azo arenes. Available nitroarenes are deoxygenated and linked selectively by the formation of NN bonds using molecular H2 without any external additives. As a result of a unique and remarkable synergy between the metal and support, a facile surface‐mediated condensation of nitroso and hydroxylamine intermediates is enabled, and the desired transformation proceeds in a highly selective manner under mild reaction conditions. The protocol tolerates a large variety of functional groups and offers a general and versatile method for the environmentally friendly synthesis of symmetric or asymmetric aromatic azo compounds.

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Section: Hydrogenative Coupling Of Nitrobenzene To Azobenzene Over Aumentioning

confidence: 90%

Gold‐Catalyzed Direct Hydrogenative Coupling of Nitroarenes To Synthesize Aromatic Azo Compounds

Liu

et al. 2014

Angewandte Chemie

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“…The former consumes stoichiometric transition metals, and the latter uses considerable nitrite salts. Both reactions are noncatalytic, and generate a large amount of inorganic waste 21. Recently, Grirrane et al.…”

Section: Photocatalytic Coupling Of Aromatic Nitro Compounds Over a Cmentioning

confidence: 99%

Copper Nanoparticles on Graphene Support: An Efficient Photocatalyst for Coupling of Nitroaromatics in Visible Light

et al. 2014

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Copper is a low-cost plasmonic metal. Efficient photocatalysts of copper nanoparticles on graphene support are successfully developed for controllably catalyzing the coupling reactions of aromatic nitro compounds to the corresponding azoxy or azo compounds under visible-light irradiation. The coupling of nitrobenzene produces azoxybenzene with a yield of 90 % at 60 8C, but azobenzene with a yield of 96 % at 90 8C. When irradiated with natural sunlight (mean light intensity of 0.044 W cm À2 ) at about 35 8C, 70 % of the nitrobenzene is converted and 57 % of the product is azobenzene. The electrons of the copper nanoparticles gain the energy of the incident light through a localized surface plasmon resonance effect and photoexcitation of the bound electrons. The excited energetic electrons at the surface of the copper nanoparticles facilitate the cleavage of the N À O bonds in the aromatic nitro compounds. Hence, the catalyzed coupling reaction can proceed under light irradiation and moderate conditions. This study provides a green photocatalytic route for the production of azo compounds and highlights a potential application for graphene.

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“…Wormlike nanowires are among the most active nanostructures, which are widely studied in both electro-catalysis and organic transformation. [28][29][30] The wavy structure and the incorporation of Mo are favorable to enhance the catalytic activity and durability, respectively. 31 Furthermore, the newly developed strategy for PtMo WNWs simplies the synthetic process for nanostructured catalysts, providing a much more practical pathway for catalytic applications.…”

Section: Introductionmentioning

confidence: 99%

A highly active worm-like PtMo nanowire for the selective synthesis of dibenzylamines

Cao

et al. 2018

RSC Adv.

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A Highly Active Nano-Palladium Catalyst for the Preparation of Aromatic Azos under Mild Conditions

Cited by 87 publications

References 37 publications

Gold‐Catalyzed Direct Hydrogenative Coupling of Nitroarenes To Synthesize Aromatic Azo Compounds

Gold‐Catalyzed Direct Hydrogenative Coupling of Nitroarenes To Synthesize Aromatic Azo Compounds

Copper Nanoparticles on Graphene Support: An Efficient Photocatalyst for Coupling of Nitroaromatics in Visible Light

A highly active worm-like PtMo nanowire for the selective synthesis of dibenzylamines

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