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Benzozaphosphorophosphine oxygen ligand and its complex, preparation method and application
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A technology of benzazepine phosphorus and phosphine oxide, which is applied in the field of metal catalysts and can solve the problems of low yield of carbon-carbon bond coupling and many by-products
Active Publication Date: 2020-05-12
SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI
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[0004] The technical problem to be solved by the present invention is to provide a kind of benzozaphosphorophosphine oxygen ligand and containing Its complexes, preparation methods and applications
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Embodiment 1
[0135]The preparation of ligand 1, the reaction scheme is as follows:
[0136]
[0137] 1. Synthesis of compound b
[0138] Take a 3L clean three-neck flask, add sulfuric acid (3×210mL, 3M), formaldehyde (125mL, 1.624mol, 4equiv) and tetrahydrofuran (700mL), then cool the above mixed system to below -20°C, and compound a (50g, 406mmol, 1.0equiv) and sodium borohydride (90g, 2.367mol, 5.8equiv) were dissolved in tetrahydrofuran and placed in a 1L clean three-neck flask, and then slowly added sulfuric acid, formaldehyde and Tetrahydrofuran mixed in the system and keep the system temperature below 0°C. In this process, sulfuric acid will be added in batches (half add at the beginning, and the remainder adds in batches during the dropwise addition). After the raw materials were added, the above system was returned to room temperature, and stirring was continued for 2 hours. TLC plate monitoring, and then the system was adjusted to strong alkalinity with potassium hydroxide a...
Embodiment 2
[0153] Ligand 1 Catalysis of Different Substrates
[0154] Take a 10mL Schlenk tube and dry it, add compound A (0.10mmol, 1.0equiv), tert-butylmagnesium chloride (0.40mmol, 4.0equiv), 1.5 hydrated nickel(II) chloride (2.5%mmol, 0.025equiv) and Ligand 1 (2.5% mmol, 0.025 equiv, nickel / ligand molar ratio is 1 / 1), pumped nitrogen three times, and sealed. Tetrahydrofuran (1 mL) was added. Cool the reaction system to -10°C for 1.5 hours, cool to room temperature, add water (10mL) and dichloromethane (10mL), separate the layers, combine the organic phases, dry over anhydrous sodium sulfate, concentrate, and use HPLC after sampling The reaction yield was detected by chromatography, and a colorless oily product was obtained by column chromatography, and the ratio of product C to by-product D was analyzed by NMR data.
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Abstract
The invention discloses a benzo polyaza and phosphole oxygen ligand and a complex containing same, a preparation method and application. The invention provides a benzo polyaza and phosphole oxygen ligand as shown in formula I and a complex containing same. A complex of the benzo polyaza and phosphole oxygen ligand and a transition metal halide enables direct coupling of carbon-carbon bonds betweenbig steric hindrance alkyl and aryl; the reaction conditions are gentle; the catalyzing efficiency is high; the coupling reaction process of the carbon-carbon bonds between big steric hindrance alkyland aryl can be extremely simplified; the practicability is high; the reaction cost can be obviously decreased, and the reaction period is reduced; the complex is free from other side products without being required in the catalyzing process. The formula refers to the description.
Description
technical field [0001] The present invention relates to the field of metal catalysts. More specifically, the present invention relates to novel benzodiazepine phosphine oxygen ligands and metal complexes containing the ligands and their highly efficient catalysis of large sterically hindered aryl halides and branched alkyl lattices. The Kumada coupling reaction of Shi's reagent, that is, a benzozaphosphorophosphine oxygen ligand and its complex, preparation method and application. Background technique [0002] The direct coupling of carbon-carbon bonds catalyzed by transition metals is an important method for the synthesis of a series of alkyl-substituted aromatic compounds, and it is widely used in pharmaceutical research. However, the existing methods still have great limitations for large steric hindrance carbon-carbon bond coupling, and the applicable high-efficiency catalysts and ligands are still rare. Especially for the formation of carbon-carbon bonds between bulky...
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