Synthesis of chiral 2,2'-bi(diphenyl phosphine)-1,1'-binaphthalene

A technology of diphenylphosphine and a synthesis method, which is applied in the field of one-step synthesis of chirality, can solve the problems of containing impurities and low yield, and achieves the effects of improved yield, simple purification method, and suitability for large-scale industrial production.

Inactive Publication Date: 2007-06-20
AOPUDISHI CHEM SCI & TECH SHANGHAI
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0018] The technical problem to be solved by the present invention is to provide a method for synthesizing chiral 2,2'-bis(diphenylphosphoryl)-1,1'-binaphthyl to solve the problem of low yield and impurity in the prior art. Defects

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  • Synthesis of chiral 2,2'-bi(diphenyl phosphine)-1,1'-binaphthalene
  • Synthesis of chiral 2,2'-bi(diphenyl phosphine)-1,1'-binaphthalene
  • Synthesis of chiral 2,2'-bi(diphenyl phosphine)-1,1'-binaphthalene

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Embodiment 1

[0032] Add 1.1 g BINOLOTf (2 mmol) and 0.064 g NiCl into a 20 ml reaction flask. 2 (dppe), 0.885 g (4 mmol) of diphenylphosphonium chloride, 5 ml of anhydrous DMF, and then 0.602 g of co-catalyst Cu powder. The reaction solution was heated to 100°C for 24 hours. The color analysis of the thin-layer silica gel plate shows that the raw materials have reacted completely. The reaction solution was cooled to room temperature and diluted with 20 ml of dichloromethane. The reaction solution was washed successively with 5% dilute hydrochloric acid, water, and saturated aqueous sodium bicarbonate solution, then separated, dried with anhydrous sodium sulfate, filtered to remove the desiccant and spin dried. After purification by silica gel chromatography, 1.05 g of pure product was obtained. The yield was 84%.

Embodiment 2

[0034] Add 2.2 g BINOLOTf (4 mmol) and 0.12 g NiCl into a 20 ml reaction flask. 2(dppe), 1.77 g (4 mmol) of diphenylphosphonium chloride, 10 ml of anhydrous DMF, and then 0.60 g of co-catalyst iron powder was added to it. The reaction solution was heated to 100°C for 24 hours. The color analysis of the thin-layer silica gel plate shows that the raw materials have reacted completely. The reaction solution was cooled to room temperature and diluted with 40 ml of dichloromethane. The reaction solution was washed successively with 5% dilute hydrochloric acid, water, and saturated aqueous sodium bicarbonate solution, then separated, dried with anhydrous sodium sulfate, filtered to remove the desiccant and spin-dried 2.0 g of pure product was obtained after purification by silica gel chromatography column. The yield was 83%.

Embodiment 3

[0036] Add 1.1 g BINOLOTf (2 mmol) and 0.084 g PdCl into a 20 ml reaction flask. 2 (DPPF), 0.885 g (4 mmol) of diphenylphosphonium chloride, 5 ml of anhydrous DMF, and then 0.302 g of co-catalyst iron powder. The reaction solution was heated to 110°C for 18 hours. The color analysis of the thin-layer silica gel plate shows that the raw materials have reacted completely. The reaction solution was cooled to room temperature and diluted with 20 ml of dichloromethane. The reaction solution was washed successively with 5% dilute hydrochloric acid, water, and saturated aqueous sodium bicarbonate solution, then separated, dried with anhydrous sodium sulfate, filtered to remove the desiccant and spin dried. After purification by silica gel chromatography, 0.92 g of pure product was obtained. The yield was 75%.

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Abstract

Synthesis of chiral 2,2'-bi(diphenyl phosphine)-1,1'-binaphthalene is carried out by reacting 2,2'-bi(ethyl methanesulfonate trifluoroacetate)-1,1'-binaphthalene with diphenyl phosphate halogen under action of complex catalyst and auxiliaries to generate the final product. It's simple, has more yield and less by-products.

Description

Technical field [0001] The present invention relates to a method for synthesizing chiral 2,2'-bis(diphenylphosphoryl)-1,1'-binaphthalene, in particular to a one-step method for synthesizing chiral 2,2'-bis( Diphenylphosphoryl)-1,1'-binaphthalene method. Background technique [0002] At the end of the 1970s, American scientist Wilkinson realized the metal-catalyzed homogeneous reaction for the first time. He realized it with the help of a simple metal ligand such as triphenylphosphonium. In the following two decades, a series of chiral catalytic reactions of great significance were invented and quickly applied to industrial production. The key to these reactions lies in efficient and highly active chiral ligands. Therefore, synthesizing and screening out ligands of this nature has become an important subject for scientists in the past two decades. Among them, chiral phosphorous ligands are one of the most important types of ligands. [0003] 2,2’-Bis(diphenylphosphoryl)-1,1’-binap...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F9/28
Inventor 罗云飞
Owner AOPUDISHI CHEM SCI & TECH SHANGHAI
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