Method for synthesizing di-ferrocene phosphine diimine structure connected with aliphatic series and benzene ring

A bis-ferrocene phosphine diimine and synthesis method technology, applied in chemical instruments and methods, metallocenes, organic chemistry, etc. Problems such as the application of iron derivatives, to achieve the effects of good yield and enantioselectivity, good application prospects, high catalytic activity and chiral induction effect

Inactive Publication Date: 2006-05-24
BEIJING INSTITUTE OF TECHNOLOGYGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0001] Ferrocene catalyst ligands have high catalytic activity and high enantioselectivity in many reactions. The usual ferrocene catalyst ligands are mostly single ferrocene derivatives. These compounds are easily Soluble in most organic solvents, it is difficult to extract and separate after the catalytic reaction, result

Method used

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  • Method for synthesizing di-ferrocene phosphine diimine structure connected with aliphatic series and benzene ring
  • Method for synthesizing di-ferrocene phosphine diimine structure connected with aliphatic series and benzene ring
  • Method for synthesizing di-ferrocene phosphine diimine structure connected with aliphatic series and benzene ring

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Experimental program
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Embodiment 1

[0023] (R)-N, N-dimethyl-1-ferrocenylethylamine (the resolution of synthesis and racemate is carried out according to the method reported by D.Marquarding et al.) was dissolved in anhydrous ether, and used Lithiation of n-butyllithium followed by quenching with diphenylphosphine chloride gave [(R,S p )-2]. will [R, S p )-2] was dissolved in anhydrous acetic anhydride, reacted at 100°C for 2h, and crystal 3 was precipitated. Crystal 3 was dissolved in methanol, excess ammonia water was added, and reacted at 80° C. for 7 h to obtain ferrocene primary amine 4 . Ferrocenylphosphinoamine compound 4 (868 mg, 2.1 mmol) and glutaraldehyde (395 mg, 4.2 mmol) were dissolved in absolute ethanol, molecular sieves (5 g) were added to reflux for 4 hours, and the ethanol was distilled off under reduced pressure to obtain a red solid. Wash with hot water to remove unreacted excess glutaraldehyde (10ml×2), dry to obtain crude product 5, dissolve 5 in ethanol and add ferrocenylphosphine amin...

Embodiment 2

[0026] Condition is the same as embodiment 1, only terephthalaldehyde is changed into m-phthalaldehyde.

Embodiment 3

[0028] Condition is the same as embodiment 1, only terephthalaldehyde is changed into o-phthalaldehyde.

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Abstract

The invention relates to a method for synthesizing planar chiral diferrocene phosphine diimide, and this ligand contains diimine and has a planar chiral diferrocene structure. This compound is condensed of planar chiral ferroceneprimary amide and various dialdehyde compounds under the existence of shrinking agent. The dialdehyde compounds can be p-phthalaldehyde, o-phthalaldehyde, m-phthalaldehyde, phenyl dialdehyde, butyl dialdehyde, glutaric dialdehyde, etc. and the method has the advantages of simple synthesizing route, simple operation, easy purification, and high yield. The invention is applied to the catalytic reactions such as aromatic ketone unsymmetrical hydrogen transfer reaction and can achieve very high yield and enantiotropic selectivity.

Description

Background technique [0001] Ferrocene catalyst ligands have high catalytic activity and high enantioselectivity in many reactions. The usual ferrocene catalyst ligands are mostly single ferrocene derivatives. These compounds are easily Soluble in most organic solvents, it is difficult to extract and separate after the catalytic reaction, resulting in a large number of expensive chiral ligands that are difficult to recycle, which greatly hinders the application of ferrocene derivatives in industrial asymmetric catalysis. Chiral bis-ferrocene phosphinodiimine ligands are a very important class of ligands. This type of ligand not only has double coordination ability, but also reduces the polarity of the bis-ferrocene structure, which is beneficial to realize recycling by utilizing the difference in solubility. [0002] Dai Huicong and others studied and synthesized a planar chiral bisferrocene Schiff base imine structure (molecular formula is as follows), and applied the ligand t...

Claims

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Application Information

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IPC IPC(8): C07F17/02
Inventor 周智明张玉梅姜飞袁浩
Owner BEIJING INSTITUTE OF TECHNOLOGYGY
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