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Ruthenium Complexes Containing Bisphosphorous Bisamino Acids and Their Applications in Catalytic Hydrogenation of Aldehydes
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A complex and catalytic hydrogenation technology, applied in organic compound/hydride/coordination complex catalysts, catalytic reactions, ruthenium organic compounds, etc.
Active Publication Date: 2017-12-08
WUHAN CATALYS TECH CO LTD
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[0003] In summary, the reduction of aldehydes has been greatly developed, but most of them occur under alkaline conditions, and the substrates are limited. Therefore, it is of great significance to develop a class of catalysts that can efficiently hydrogenate and reduce aldehydes under neutral conditions. Significance
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Embodiment 1
[0083] Metal ruthenium complexes Ru(PPh 3 ) 2 (Gly) 2 preparation of
[0084] RuCl 2 (PPh 3 ) 3 (0.479g, 0.5mmol), glycine (90mg, 1.2mmol) were dissolved in 20mL ethanol, heated and stirred at 50°C for 3h, cooled, filtered, the filtrate was spin-dried, dissolved in dichloromethane, passed through diatomaceous earth, and the obtained filtrate was spin-dried , to obtain a yellow solid (150 mg). ESI-HRMS Calculated for C 31 h 35 N 2 o 4 P 2 Ru + ([M+H] + ):663.1110, found663.1118.
Embodiment 2
[0086] Metal ruthenium complex Ru(S-BINAP)(S-phgly) 2 preparation of
[0087] [RuCl 2 (benzene)] 2 (50mg, 0.1mmol) and S-BINAP (130mg, 0.21mmol) were mixed, pumped into a nitrogen atmosphere, added 3mL N,N-dimethylformamide, heated and stirred at 110°C for 10min, cooled to room temperature, added sodium phenylglycinate (103mg, 0.6mmol) in 6mL of methanol solution, stirred at 40°C for 3h, poured the reaction solution into 50mL of ice water, stirred for 10min, filtered out the precipitate, washed both sides with water, and purified the obtained solid by column chromatography to obtain a yellow solid (148mg, Yield 72%). ESI-HRMS Calculated for C 40 h 39 N 2 o 4 P 2 Ru + ([M+H] + ):775.1423, found745.1432.
Embodiment 3
[0089] Metal ruthenium complexes Ru(DPPP)(S-phgly) 2 preparation of
[0090] [RuCl 2 (benzene)] 2 (250mg, 0.5mmol) and 1,3-bis(diphenylphosphino)propane (412mg, 1mmol) were mixed, pumped into a nitrogen atmosphere, added 15mL N,N-dimethylformamide, heated and stirred at 110°C for 2h , cooled to room temperature, adding sodium glycinate (290mg, 3mmol) in 20mL methanol solution, stirred at room temperature overnight, poured the reaction solution into 100mL ice water, extracted three times with dichloromethane (50mL×3), dried, and spin-dried to obtain a solid Purification by column chromatography gave a yellow solid (395 mg, yield 60%). The single crystal structure obtained by recrystallization is shown in the attached figure.
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Abstract
The invention belongs to the technical field of organic chemistry, and particularly relates to a bi-phosphorus bi-amino acid containing ruthenium complex and catalysis of the complex to hydrogenation reduction of aldehyde. The complex can be obtained from simple phosphine ligands and amino carboxylate via simple preparation. The ruthenium catalyst efficiently carries out catalytic reduction of the aldehyde to alcohol on the neutrality condition. The catalyst has the advantages of being easy to prepare, high in catalytic efficiency, good in stability and the like, thereby having potential industrial application value.
Description
technical field [0001] The invention belongs to the technical field of organic chemistry, and in particular relates to a bisphosphorus-containing bisamino acid ruthenium complex and the catalytic effect of the complex in the hydrogenation reduction reaction of aldehydes. Background technique [0002] The traditional reduction method of aldehydes mainly uses equivalent metal reagents, such as sodium borohydride. The metal reagents required for this type of reduction reaction are relatively expensive, and post-processing is troublesome. The method of catalytic hydrogenation is a relatively green reduction method. For aldehydes and ketones containing carbonyls, the most widely studied is Noyori's ruthenium-bisphosphorous diamine catalyst. This catalytic system is extremely efficient and is mainly used in the production of ketones. asymmetric hydrogenation reaction, but there are few reports on the catalytic reduction of aldehydes. The reason may be that the catalyst system need...
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