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Phosphinidene amide and transition metal complex catalyst and its synthesis process and application in C-C and C-N bond forming reaction

A transition metal, phosphine amide technology, applied in the direction of organic compound/hydride/coordination complex catalyst, physical/chemical process catalyst, chemical instrument and method, etc., can solve the problems of high price, difficult preparation, sensitivity, etc., Achieve the effects of easy preparation, simple synthesis method, good water resistance and air stability

Inactive Publication Date: 2003-05-14
SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Most of the ligands are trivalent phosphine compounds, which are expensive, difficult to prepare, and sensitive to air and moisture

Method used

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  • Phosphinidene amide and transition metal complex catalyst and its synthesis process and application in C-C and C-N bond forming reaction
  • Phosphinidene amide and transition metal complex catalyst and its synthesis process and application in C-C and C-N bond forming reaction

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1 2

[0038] The synthesis (hereinafter referred to as L 1 )

[0039] Add 35ml of anhydrous benzene and 21.4ml (0.2mol) of o-methylaniline to a 250ml three-neck flask dried under nitrogen protection, stir magnetically, slowly add 20ml of benzene and 17.9ml of diphenylphosphine chloride (0.1mol) dropwise under ice bath The mixed solution was stirred at room temperature for 2 hours after the dropwise addition, and a white solid was formed in the system at this time. After filtration, the filtrate was distilled off at atmospheric pressure to remove benzene to obtain a viscous liquid, which was chromatographed on a basic alumina column to obtain 19.75 g of a white solid with a yield of 67.9%.

[0040] 1 H NMR (300MHz, CDCl3 )δ7.49-7.36 (m, 10H), 7.29-7.24 (m, 1H), 7.13-7.08 (m, 2H), 6.80-6.74 (m, 1H), 4.25 (d, J=8.1Hz, 1H) , 2.21(s, 3H); 13 C NMR (75MHz, CDCl 3 )δ 140.3 (d, J = 12.7Hz), 131.1 (d, J = 22.5Hz), 130.3 (d, J = 1.5Hz), 129.0, 128.6, 128.5, 127....

Embodiment 2 2

[0041] The synthesis (hereinafter referred to as L 2 )

[0042] Add diisopropylamine (0.1mol) and 14.1ml (0.1mol) of triethylamine to a 250ml three-neck flask under nitrogen protection, add 17.9ml diphenylphosphine chloride (0.1mol) dropwise under magnetic stirring, and heat after the dropwise addition reflow. A large amount of white precipitate formed at the bottom of the flask, which was filtered off, and the filtrate was subjected to basic alumina column chromatography and rinsed with petroleum ether to obtain 21.73 g of white solid, with a yield of 76.2%.

[0043] 1 H NMR (300MHz, CDCl 3 )δ7.53-7.47(m, 4H), 7.34-7.30(m, 6H), 3.39(m, 2H), 1.08(d, J=6.3Hz, 12H).

Embodiment 3 2

[0044] The synthesis (hereinafter referred to as L 3 )

[0045] Add 1.5ml (14mmol) of o-methylaniline and 10ml of anhydrous THF to a 100ml three-necked bottle under nitrogen protection, and inject 10ml of n-butyllithium (1.6mol / l, 16mmol) under magnetic stirring. hot. After the system was stabilized, it was heated to reflux for 2 hours, and after cooling to room temperature, a mixed solution of 10 ml of anhydrous anhydrous THF and 2.6 ml of di-tert-butylphosphine chloride (14 mmol) was added dropwise. After the dropwise addition, it was heated to reflux for 2 hours, a white precipitate was formed at the bottom of the flask, the solid was filtered off, and the filtrate was subjected to basic alumina column chromatography and rinsed with petroleum ether to obtain 2.98 g of a white solid, with a yield of 84.9%. 1 H NMR (300MHz, CDCl 3 )δ7.39-7.24(m, 1H), 7.10-7.03(m, 2H), 6.69-6.63(m, 1H), 3.92(d, J=10.2Hz, 1H), 1.14(d, J=12.0Hz ,18H); 13 C NMR (75M...

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Abstract

The present invention relates to a catalyst for C-C and C-N bond forming reaction and its synthesis and application. The catalyst has the structure formula of M-Ln, where M is transition metal including Pa, Ni, Co, Ru and Rh; and L is phosphinidene amide ligand. The phosphinidene amide ligand of the catalyst has the features of easy preparation and stability in air. The catalyst can catalyze various aromatic amine and has important application value in pharmaceutical industry.

Description

technical field [0001] The invention relates to a kind of complex formed by a phosphoramidite having an N-P bond and a transition metal as a catalyst, a synthesis method and an application in C-C, C-N bond forming reactions. Background technique [0002] With the development of organometallic chemistry, reactions catalyzed by organotransition metals have increasingly become efficient methods for the formation of carbon-carbon bonds and carbon-heteroatom bonds. Catalysts for these reactions generally use complexes of transition metals and ligands, and usually require organic phosphine as a ligand to stabilize the central metal or improve the activity of the metal. Therefore, the choice of ligand is often a key issue in the success of a reaction. [0003] The coupling reaction between metal reagents and aryl halides is precisely the most concise and effective method to form carbon-carbon bonds. Since the discovery of the coupling of Grignard reagents with aryl halides in 197...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): B01J31/24
Inventor 张兆国成江王锋徐建华
Owner SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI
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