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Nitrogen phosphine ligand, preparation method thereof and application of nitrogen phosphine ligand in aryl ethylene hydroformylation reaction
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A ligand, nitrogen phosphine technology, applied in the field of homogeneous catalyst ligands, can solve the problems of low regioselectivity and poor reactivity, and achieve the effect of simple operation process
Pending Publication Date: 2022-01-21
FUDAN UNIV
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In subsequent studies, new water-soluble phosphine ligands with different structures were developed, such as BISBIS, BINAS, NORBOS, Sulfonated-Xantphos, phosphine-modified polyethylene glycol-based ligands, etc. In the acylation reaction, there are problems of poor reactivity and low regioselectivity
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Embodiment 1
[0046] Embodiment 1, the preparation of ligand L1
[0047]
[0048] Step 1, add 1a (2mmol), 2 (2mmol) and DCM (4mL) to the reaction flask, add TEA (8mmol) at 0°C, then move to room temperature and react for 24h, evaporate the solvent and perform column separation to obtain the product (3a : 83%).
[0049] Step 2, THF (2mL) dissolved 3a (1mmol), then LiOH·H 2 O (1.5mmol) was dissolved in 1ml of water and added to the reaction flask. When the raw materials were completely reacted, 5% HCl was added to adjust the pH to 2. After THF was distilled off, it was extracted with DCM. Na 2 SO 4 After drying, the solvent was evaporated to obtain a colorless oily product, which was then washed with THF (1ml) and H 2 O (1mL) was dissolved, NaOH (1mmol) was added, stirred at room temperature for 2h, and the solvent was evaporated to obtain the product (L1: 95%).
Embodiment 2
[0050] Embodiment 2, the preparation of ligand L5
[0051]
[0052] Step 1, add 4a (2mmol), 2 (2mmol) and THF (4mL) into the reaction flask, add TEA (8mmol) at 0°C, then move to room temperature and react for 24h, evaporate the solvent and perform column separation to obtain the product (5a : 89%).
[0053] Step 2, add NaI (1.5mmol), 5a (1mmol) and acetone to the reaction flask, heat to reflux until the reaction is complete, evaporate the solvent to dryness and wash the product with acetone to obtain (L5: 83%).
Embodiment 3
[0054] Embodiment 3, the preparation of ligand L6
[0055]
[0056] Step 1, add 4b (2mmol), 2 (2mmol) and THF (4mL) into the reaction flask, add TEA (8mmol) at 0°C, then move to room temperature and react for 24h, evaporate the solvent and perform column separation to obtain the product (5b : 85%).
[0057] Step 2, add NaI (1.5mmol), 5b (1mmol) and acetone to the reaction flask, heat to reflux until the reaction is complete, evaporate the solvent and wash the product with acetone to obtain (L6: 81%).
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technical field [0001] The invention belongs to the technical field of homogeneous catalyst ligands, and in particular relates to a nitrogen phosphine ligand and its preparation method and application in arylethene hydroformylation. Background technique [0002] Hydroformylation refers to the chemical process in which olefins undergo oxidative addition reaction with carbon monoxide and hydrogen under the action of transition metal catalysts to obtain the product aldehyde. Hydroformylation is currently the largest homogeneously catalyzed reaction in industrial applications. The metal components in hydroformylation catalysts are mainly Rh, Co and Ru. Ligands are the core issue in the design of hydroformylation catalysts. The structure of ligands affects the chemoselectivity, regioselectivity and stereoselectivity of the reaction process. Rh metal catalysts complexed with organophosphine ligands have excellent catalytic performance in olefin hydroformylation. [0003] For th...
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