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Method for catalyzing non-tension non-polar carbon-carbon single bond hydrogenolysis of dicarbonyl compound
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A technology that catalyzes hydrogenolysis and compounds, applied in the chemical industry, can solve problems such as harsh reaction conditions and expensive catalysts, and achieve the effects of mild reaction conditions, wide application range of reactions, and strong controllability
Active Publication Date: 2021-08-03
FUDAN UNIV
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[0003] The above method of hydrogenolysis of carbon-carbon bonds is limited on the substrate, the price of the catalyst is more expensive, and the reaction conditions are relatively harsh
Since carbonyl groups (including alkenes) are more easily reduced than unstrained nonpolar carbon-carbon single bonds, selective carbon-carbon single-bond hydrogenolysis reactions of saturated and unsaturated ketones have not been reported so far
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Embodiment 1
[0024] Carbon-carbon bond hydrogenolysis of 1,3,5-triphenyl-1,5-pentanedione, the chemical structures of reactants and products are as follows:
[0025]
[0026] Under nitrogen protection, add raw material 1,3,5-triphenyl-1,5-pentanedione (0.50mmol), benzhydryl alcohol (0.55mmol) and catalyst Y[N(SiMe 3 ) 2 ] 3 (2mol%), reacted in 2mL toluene at 60°C for 12h, and the isolated yields of acetophenone and 1,3-diphenyl-1-propanone were 79% and 80%, respectively.
Embodiment 2
[0028] Under nitrogen protection, raw material 1,3,5-triphenyl-1,5-pentanedione (0.50mmol), triethylsilane (0.55mmol) and catalyst Sm[CH 2 (TMS)] 3 (5mol%), reacted in 2mL of toluene at 60°C for 10h, and the isolated yields of acetophenone and 1,3-diphenyl-1-propanone were 80% and 83%, respectively.
Embodiment 3
[0030] Under nitrogen protection, raw materials 1,3,5-triphenyl-1,5-pentanedione (0.50mmol), diisobutylamine (1.0mmol) and catalyst Sm[CH 2 (TMS)] 3 (5mol%), reacted in 2mL of toluene at 60°C for 12h, the isolated yields of acetophenone and 1,3-diphenyl-1-propanone were 71% and 74%, respectively.
[0031] Acetophenone: 1 H NMR (400MHz, CDCl 3 )δ7.98-7.95(m,2H),7.58-7.55(m,1H),7.48-7.44(m,2H),2.61(s,3H);
[0032] 1,3-Diphenyl-1-propanone: 1 H NMR (400MHz, CDCl 3 )δ7.99-7.97(m,2H),7.59-7.56(m,1H),7.49-7.46(m,2H),7.34-7.21(m,5H),3.33(t,J=7.7Hz,2H) ,3.11-3.07(m,2H).
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Abstract
The invention belongs to the technical field of chemical engineering, and particularly relates to a method for catalyzing non-tension non-polar carbon-carbon single bondhydrogenolysis of a dicarbonyl compound. According to the method, in a rare earthcatalysissystem, a secondary alcohol (amine) compound or hydrosilyane is used as a hydrogen source, and non-tension carbon-carbon single bonds of diketone and ketone ester are subjected to hydrogenolysis to form monoketone (ester). The method is a first carbon-carbon bond hydrogenolysis reaction of ketone, and the reaction has the advantages of good atom economy, high position selectivity and chemical selectivity, mild conditions, simplicity and convenience in operation, strong functional group tolerance and the like. Diketone and ketone ester are wide in source, and application is wide when diketone and ketone ester are converted into monoketone (ester).
Description
technical field [0001] The invention belongs to the technical field of chemical industry, and in particular relates to a method for rare earth catalyzed hydrogenolysis of a non-tensioned non-polar carbon-carbon single bond far away from a carbonyl group. Background technique [0002] Selective hydrogenolysis of carbon-carbon single bonds is one of the most atom-economical and facile methods for dismantling organic molecules. It has a wide range of applications in organic synthesis, polymers, biomass and petroleumcracking (Topics in Catalysis.2018, 61, 183-198). In industry, heterogeneous cracking of petroleum usually requires high temperature (300–450°C) and high pressure (100–180 atm) conditions (Chemcatchem.2012, 4, 292-306). However, activation of unstrained carbon-carbon bonds by homogeneous systems is relatively inconvenient and generally requires one of the C(sp 3 ) to a heteroatom or two carbonyl groups, or some specific transformations that require a stoichiometri...
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