102-50-1Relevant articles and documents
Palladium on Polydopamine: Its True Potential in Catalytic Transfer Hydrogenations and Heck Coupling Reactions
Kunfi, Attila,Szabó, Vivien,Mastalir, ágnes,Bucsi, Imre,Mohai, Miklós,Németh, Péter,Bertóti, Imre,London, Gábor
, p. 3236 - 3244 (2017)
The application of Pd–polydopamine and magnetic Fe3O4@Pd–polydopamine catalysts in catalytic transfer hydrogenation reactions and the Heck arylation is reported. The reduction of a wide range of aromatic nitro-compounds bearing both electron-donating and -withdrawing substituents to the corresponding anilines could be efficiently performed, although the reduction of carbonyl compounds was found to be less general. In the latter case, only aromatic ketones could be reduced to the corresponding alcohols, whereas aldehyde substrates were unaffected, which may be owing to their reaction with the catalyst support leading to catalyst deactivation. By using magnetic Fe3O4@Pd–polydopamine system, facilitated catalyst recovery and reuse for five consecutive cycles without considerable loss of activity in nitro-group reduction. The efficiency of the catalyst in Heck reactions was comparable to that in transfer hydrogenation, however, no catalytic activity was observed upon reuse in this case, likely as a result of metal leaching. We also explored tandem Heck reaction/catalytic transfer hydrogenation sequences, however, the two reactions showed limited compatibility under the applied conditions.
Metal-free Reduction of Nitro Aromatics to Amines with B 2 (OH) 4 /H 2 O
Chen, Danyi,Zhou, Yanmei,Zhou, Haifeng,Liu, Sensheng,Liu, Qixing,Zhang, Kaili,Uozumi, Yasuhiro
, p. 1765 - 1768 (2018)
A metal-free reduction of nitro aromatics mediated by diboronic acid with water as both the hydrogen donor and solvent under mild conditions has been developed. A series of aromatic amines were obtained with good functional group tolerance and in good yields.
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
, p. 3898 - 3904 (2017)
An unprecedented palladium-catalyzed chemoselective reduction and reductive amination of nitroarenes with water as a hydrogen source mediated by diboronic acid have been discovered. A series of aryl amines containing various reducible functional groups were obtained in good to excellent yields.
Transition-metal-free access to primary anilines from boronic acids and a common +NH2 equivalent
Voth, Samantha,Hollett, Joshua W.,Mccubbin, J. Adam
, p. 2545 - 2553 (2015)
Diversely substituted anilines are prepared by treatment of functionalized arylboronic acids with a common, inexpensive source of electrophilic nitrogen (H2N-OSO3H, HSA) under basic aqueous conditions. Electron-rich substrates are found to be the most reactive by this method. However, even moderately electron-poor substrates are well tolerated under the room temperature conditions. Sterically hindered substrates appear to be equally effective compared to unhindered ones. Highly electron-deficient substrates afford product in very low yields at room temperature, but moderate to good yields are obtained at refluxing temperatures. Our method is also amenable to electrophilic amination of several common boronic acid derivatives (e.g., pinacol esters). We demonstrate that it can be combined with metal-halogen exchange reactions or a variety of directed ortho metalation protocols in a "one-pot" sequence for the synthesis of aromatic amines with unique substitution patterns. DFT studies, in combination with experimental results, suggest that the reaction occurs via base-mediated activation of HSA, followed by 1,2 aryl B-N migration. This mode of activation appears to be critical for the success of the reaction and allows, for the first time, a general, electrophilic amination of boronic acids at ambient temperature.
Methoxy aniline compound and synthesis method thereof
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Paragraph 0027; 0030-0032; 0041-0042, (2021/05/19)
The invention mainly relates to a preparation method of anisidine. According to the technical scheme, under the promotion of the photocatalyst and blue light, in the argon atmosphere, nitro compounds and methanol generate methoxyaniline, wherein products and additional products with stable molecular structures and excellent chemical properties are prepared, wherein a photocatalyst and a blue light source are used in the method, and a new path is provided for synthesis of methoxyaniline compounds. The method has the characteristics of mild reaction conditions, simple reaction system, less reaction equipment, simplicity and convenience in experimental operation and the like. The methoxyaniline derivative and the synthetic method thereof can be applied to a plurality of industrial production fields of dyes, pesticides, medicines, rubber additives and the like. The method is particularly suitable for scientific research, development and utilization of efficient and selective synthesis of methoxyaniline compounds by a one-pot method.
Method for reducing aromatic nitro into arylamine
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Paragraph 0113-0116, (2020/07/15)
The invention relates to a method for reducing aromatic nitro to arylamine. The method comprises the following steps: (1) taking an aromatic nitro compound as a raw material, water as a hydrogen source, a palladium compound, cheap and easy to obtain, as a catalyst and tetrahydroxydiboron as an additive to reduce nitro to obtain a product; (2) taking the aromatic nitro compound as the raw material, a copper salt, cheap and easy to obtain, as the catalyst, the tetrahydroxydiboron as the additive to reduce the nitro to obtain a product; and (3) taking the aromatic nitro compound as the raw material, water as the hydrogen source, and the tetrahydroxydiboron as the additive, without needing a metal catalyst, to reduce the nitro to obtain a product. A preparation method for the arylamine, which is provided by the invention, is mild in reaction condition, low in costs, environment-friendly, high in yield, and suitable for industrial production.
Synthesis method of aminobenzoate compound (by machine translation)
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Paragraph 0094-0098; 0137-0139, (2020/08/09)
The synthesis method comprises the following steps: carrying out a hydrogenation reduction reaction of a nitroanisole compound with a carbon-coated nickel containing alkaline earth metal in a hydrogen atmosphere; wherein the shell layer is a graphitized carbon layer containing alkaline earth metal, nitrogen and oxygen. To the method, the alkaline earth metal-containing carbon-coated nano composite material is used as a catalyst, the carbon material and the nickel nanoparticles cooperate to play a good catalytic effect, and the alkaline earth metal of the shell layer further synergistically improves the catalytic performance of the material. (by machine translation)
Synthesis method of amino-anisole compound
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Paragraph 0147-0149, (2020/08/09)
The invention provides a synthesis method of an amino-anisole compound. The synthesis method comprises the following steps: taking a carbon-coated nickel nano composite material containing alkali metals as a catalyst, and catalyzing a hydrogenation reduction reaction of a nitro-anisole compound in a hydrogen atmosphere; wherein the nano composite material contains a core-shell structure with a shell layer and an inner core, the shell layer is a graphitized carbon layer containing alkali metals, nitrogen and oxygen, and the inner core is nickel nano particles. According to the method, the nanocomposite material is used as a catalyst; a carbon material and the nickel nano particles generate a synergistic effect and a good catalytic effect, the alkali metals of the shell layer further synergistically improve the catalytic performance of the nano composite material, and the catalyst is used for hydrogenation reduction of nitro-anisole compounds to synthesize amino-anisole compounds, and has excellent activity, selectivity and safety.
Synthesis method of amino-anisole compound
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Paragraph 0057; 0154-0156, (2020/08/09)
The invention provides a synthesis method of an amino-anisole compound. The synthesis method comprises the following steps: taking a carbon-coated nickel nano composite material containing alkali metals as a catalyst, and catalyzing a hydrogenation reduction reaction of a nitro-anisole compound in a hydrogen atmosphere; wherein the nano composite material contains a core-shell structure with a shell layer and an inner core, the shell layer is a graphitized carbon layer containing alkali metals and oxygen, and the inner core is nickel nano particles. According to the method, the nano compositematerial is used as a catalyst; a carbon material and the nickel nano particles generate a synergistic effect and a good catalytic effect, the alkali metals of the shell layer further synergisticallyimprove the catalytic performance of the nano composite material, and the catalyst is used for hydrogenation reduction of nitro-anisole compounds to synthesize amino-anisole compounds, and has excellent activity, selectivity and safety.
Direct synthesis of anilines and nitrosobenzenes from phenols
St Amant,Frazier,Newmeyer,Fruehauf,Read De Alaniz
, p. 5520 - 5524 (2016/07/06)
A one-pot synthesis of anilines and nitrosobenzenes from phenols has been developed using an ipso-oxidative aromatic substitution (iSOAr) process. The products are obtained in good yields under mild and metal-free conditions. The leaving group effect on reactions that proceed through mixed quionone monoketals has also been investigated and a predictive model has been established.
