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2,2',6,6'-tetra substituted nitrogen phosphine ligand and its synthesis method

A synthetic method and four-substitution technology, applied in 2 fields, can solve the problems that the same or similar literature reports have not yet been found, and achieve the effects of high reactivity and stereoselectivity, good application prospects, and simple preparation methods

Inactive Publication Date: 2008-09-03
SHANGHAI JIAOTONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] 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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  • 2,2',6,6'-tetra substituted nitrogen phosphine ligand and its synthesis method
  • 2,2',6,6'-tetra substituted nitrogen phosphine ligand and its synthesis method
  • 2,2',6,6'-tetra substituted nitrogen phosphine ligand and its synthesis method

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Experimental program
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Embodiment 1

[0022] 1. Preparation of 2,2',6,6'-tetranitrobiphenyl

[0023] Pretreatment copper powder: take copper powder (5.0g, 78mmol) and join in 2% iodine / acetone solution 20ml, stir for ten minutes, suction filter, then join in the mixed solution 20ml of acetone:hydrochloric acid=1:1, Stir for ten minutes, filter with suction, and dry in vacuo. Add 2,6-dinitrochlorobenzene (3.04g, 15mmol) and copper powder (2.88g, 45mmol) into a 250ml round-bottomed flask and mix well. Under the protection of nitrogen, heat the oil bath to 180°C and stir for 2 hours. After the reaction, the solid in the bottle was broken up, dissolved with 20ml of ethyl acetate, the solid was filtered out, the filtrate was collected, and rotary evaporated. Recrystallized with ethyl acetate:petroleum ether=10:1, precipitated light yellow needle-like crystals, filtered with suction, collected the crystals, and obtained the product with a yield of 63.9%.

[0024] 1 H NMR (400 MHz, CDCl 3 ): 7.89 (t, 2H, J=8.0 Hz, Ar...

Embodiment 2

[0034] 1.2,2 ', 6, the preparation of 6'-tetranitrobiphenyl (same as embodiment one)

[0035] 2.2,2 ', 6, the preparation of 6'-tetraaminobiphenyl (same as embodiment one)

[0036] 3. Preparation of 2,2',6,6'-tetraphenylphosphorylaminobiphenyl

[0037] 2,2',6,6'-Tetraaminobiphenyl (107.90mg, 0.5mmol) was dissolved in 10ml of tetrahydrofuran, the reaction system was cooled to -30°C, and a n-butyllithium solution in n-hexane was added dropwise to the system ( 2.57M, 0.78ml), and stirred at this temperature for 2 hours, then added diphenyl-o-chloro (0.45ml, 2.5mmol) dropwise, the temperature rose to 25°C, stirred for 5 hours, filtered the precipitate, evaporated THF . Ethyl acetate / petroleum ether=1:5 column chromatography, the target product was obtained with a yield of 83%.

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Abstract

The present invention relates to 2, 2', 6, 6'-tetrasubstituent nitrogen phosphine ligand and its synthesis process. The 2, 2', 6, 6'-tetrasubstituent nitrogen phosphine ligand possesses the structure as shown, and has synthesis process including the following steps: 1. coupling 2, 6-dinitro chloro benzene as initial material to obtain 2, 2', 6, 6'-tetranitro diphenyl; 2. Pd-C catalyzed hydrogenation of 2, 2', 6, 6'-tetranitro diphenyl to obtain 2, 2', 6, 6'-tetramino diphenyl; and 3. reacting 2, 2', 6, 6'-tetramino diphenyl and diphenyl phosphorus chloride to obtain 2, 2', 6, 6'-tetradiphenyl phosphino amino diphenyl. The 2, 2', 6, 6'-tetrasubstituent nitrogen phosphine ligand itself is compound without chirality and may have chirality introduced to obtain bimetallic chiral catalyst with single configuration, and the catalyst may be applied in multiple metal catalyzed asymmetric reaction and possesses very high reaction activity and stereo selectivity.

Description

technical field [0001] The invention relates to an achiral ligand and a synthesis method thereof, in particular to a 2,2',6,6'-tetrasubstituted nitrogen phosphine ligand used in asymmetric catalytic reactions and a synthesis method thereof. technical background [0002] The asymmetric catalytic method is a better way to obtain chiral drugs with a single enantiomer, which can achieve a large number of chiral compounds from a small amount of chiral catalysts, reduce or even avoid the generation of invalid bodies, which is not only beneficial to environmental protection, but also can Achieving good atom economy can also avoid the cumbersome splitting of the racemate. [0003] Designing and synthesizing chiral catalysts with high selectivity and high catalytic activity is the key to asymmetric catalytic synthesis. In transition metal-catalyzed asymmetric reactions, the chiral ligands coordinated to the metal play a decisive role in the reactivity and enantioselectivity. [000...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F9/50
CPCC07F9/46
Inventor 张万斌谢芳房芳
Owner SHANGHAI JIAOTONG UNIV