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C2-symmetrical chirality bis ruthenium ligand and its synthesis method

A synthesis method and ruthenocene technology, which are applied in the field of C2-symmetric chiral ruthenocene ligands and their synthesis, can solve the problems that the same or similar literature reports have not been found, and achieve high reactivity and stereoselectivity, The effect of good application prospects

Active Publication Date: 2006-12-13
SHANGHAI JIAO TONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] Found through literature search to prior art, have not found the same or similar literature report as the subject of the present invention so far

Method used

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  • C2-symmetrical chirality bis ruthenium ligand and its synthesis method
  • C2-symmetrical chirality bis ruthenium ligand and its synthesis method
  • C2-symmetrical chirality bis ruthenium ligand and its synthesis method

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Embodiment 1

[0029] 1. Preparation of 1,3-cyclocene

[0030] Take 50mL of bicyclocene in a 150mL one-necked flask, under N 2 Raise the temperature to 180-200°C under protection, let the steam pass through the rectification column, collect the fraction at 40-42°C, and obtain a colorless transparent liquid, which is directly used in the next reaction.

[0031] 2. Preparation of ruthenocene

[0032] RuCl 3 *nH 2 O (5.26g, 20mmol) was dissolved in absolute ethanol (250mL), cyclocene (25mL) was added dropwise at room temperature, and then Zn powder was added in batches. The resulting gray suspension was stirred for 2 h, filtered, and the filter cake was washed with a large amount of toluene. The toluene phase was decolorized with activated carbon, dried over anhydrous magnesium sulfate, and the solvent was recovered under reduced pressure to obtain 4.3 g of light green crystals, y=85.3%.

[0033] 1 H NMR (400MHz, CDCl 3 ): δ4.55(s, 10H).

[0034] 3. Preparation of 1,1'-dicarboxyruthenoc...

Embodiment 2

[0045] 1. Preparation of 1,3-cyclocene

[0046] Take 50mL of bicyclocene in a 150mL one-necked flask, under N 2 Raise the temperature to 180-200°C under protection, let the steam pass through the rectification column, collect the fraction at 40-42°C, and obtain a colorless transparent liquid, which is directly used in the next reaction.

[0047] 2. Preparation of ruthenocene

[0048] RuCl 3 *nH 2 O (5.26g, 20mmol) was dissolved in absolute ethanol (250mL), cyclocene (25mL) was added dropwise at room temperature, and then Zn powder was added in batches. The resulting gray suspension was stirred for 2 h, filtered, and the filter cake was washed with a large amount of toluene. The toluene phase was decolorized with activated carbon, dried over anhydrous magnesium sulfate, and the solvent was recovered under reduced pressure to obtain 4.3 g of light green crystals, y=85.3%.

[0049] 1 H NMR (400MHz, CDCl 3 ): δ4.55(s, 10H).

[0050] 3. Preparation of 1,1'-dicarboxyruthenoc...

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Abstract

The invention relates the synthesis of C2-symmetry chirality bis ruthenium ligand. The method comprises the following steps: 1 using dicyclopentadiene as raw material, carrying out depolymerisation, and getting cyclopentadiene; 2 carrying out reaction of cyclopentadiene and ruthenic chloride, and getting bis ruthenium; 3 getting 1, 1' - dicarboxyl bis ruthenium; 4 the dicarboxyl bis ruthenium and oxalyl chloride reacting in carrene, and getting 1, 1'- dichloro carbonyl bis ruthenium; 5 1, 1'- dichloro carbonyl bis ruthenium and beta- amino alcohol reacting, getting acidamide compound, then it reacting with methane sulfonyl chlo-ride, and getting 1, 1'- dioxazoline bis ruthenium; 6 1, 1'- dioxazoline bis ruthenium and secondary butyl lithium reacting, then them reacting with biphenyl phosphorus chlorides, and getting C2- dioxazoline 2, 2'- biphenyl phosphino bis ruthenium. The ligand from the invention can be used in metallic catalysis asymmetric reaction, and the ligand has the good reaction active and stereoselectivity.

Description

technical field [0001] The invention relates to a chiral ligand in the technical field of chemical engineering and a synthesis method thereof, in particular to a C ligand used in an asymmetric catalytic reaction. 2 -Symmetrical chiral ruthenocene ligands and methods for their synthesis. technical background [0002] The rapid rise of the chiral drug industry is mainly due to the great development of asymmetric synthesis methodology research, and in turn, the chiral drug industry has promoted the research of asymmetric synthesis methodology. Asymmetric catalytic organic synthesis is one of the most effective and beneficial methods to obtain chiral compounds. In asymmetric catalytic organic synthesis, the key to high reactivity and high enantioselectivity lies in the structure of chiral phosphine ligands. Therefore, the development of chiral phosphine ligands has always been a key research area of ​​concern in academia and industry. [0003] In 1965, Wilkinson et al. used R...

Claims

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Application Information

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IPC IPC(8): C07F17/02C07F9/653B01J31/24
Inventor 张万斌谢芳刘德龙商健华更红
Owner SHANGHAI JIAO TONG UNIV
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