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Gold complex containing diphosphine ortho-position carborane ligand as well as preparation method and application of gold complex

A gold complex and carborane technology, which is applied in the field of complex synthesis, can solve the problems of high catalyst equivalent, catalyst instability, and long reaction time, and achieve low catalyst consumption, simple and green preparation method, and fast reaction rate Effect

Active Publication Date: 2020-07-10
SHANGHAI INST OF TECH
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  • Description
  • Claims
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Problems solved by technology

[0004] In summary, there are some reports on the method of synthesizing disubstituted thiazoles, but all have its defects, such as the instability of the catalyst, the high equivalent weight of the catalyst, the reaction needs additives, the reaction time is long, and the temperature is high. its application

Method used

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  • Gold complex containing diphosphine ortho-position carborane ligand as well as preparation method and application of gold complex
  • Gold complex containing diphosphine ortho-position carborane ligand as well as preparation method and application of gold complex
  • Gold complex containing diphosphine ortho-position carborane ligand as well as preparation method and application of gold complex

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] Example 1: Synthesis of gold complex 1 and its application in the synthesis of 2,4-disubstituted thiazole compounds by catalyzing the reaction of terminal alkyne and thioamide

[0033] At 0℃, add n-BuLi (2.2mmol) n-hexane solution dropwise to o-C containing ortho carborane 2 B 10 H 12 (1.0mmol) in ether solution, continue to stir for 30 minutes after the dropwise addition, slowly rise to room temperature and continue to react for 30 minutes, then add halophosphine ClPPh 2 (2.2mmol), continue to react at room temperature for 2 hours, and then add AuCl (1.0mmol) to the reaction system at room temperature and continue to react for 3 hours. After the reaction is over, stand still and filter, drain the solvent under reduced pressure, and wash the crude product with ether , And drain to obtain the target product 1 (yield 85%), the reaction formula is:

[0034]

[0035] 1 H NMR(400MHz, CDCl 3 , 25°C): δ=7.79-7.67 (m, 8H), 7.55-7.47 (m, 12H). Elemental analysis theoretical value C 2...

Embodiment 2

[0041] Example 2: Synthesis of gold complex 2

[0042] At 0℃, add n-BuLi (2.5mmol) n-hexane solution dropwise to o-C containing ortho carborane 2 B 10 H 12 (1.0mmol) in the ether solution, after the dropwise addition, continue to stir for 30 minutes, slowly rise to room temperature and continue the reaction for 30 minutes, then add the halogenated phosphine ClP(4-MeO-C 6 H 4 ) 2 (2.5mmol), continue to react at room temperature for 2 hours, and then add AuCl (1.0mmol) to the reaction system at room temperature and continue to react for 5 hours. After the reaction is over, stand still and filter, drain the solvent under reduced pressure, and wash the crude product with ether , And drain to obtain the target product 2 (yield 80%), the reaction formula is:

[0043]

[0044] 1 H NMR(400MHz, CDCl 3 , 25°C): δ=7.72-7.65 (m, 8H), 7.60-7.51 (m, 8H), 3.36 (s, 12H). Elemental analysis theoretical value C 30 B 10 H 38 O 4 P 2 AuCl: C 41.65, H 4.43; experimental value: C 41.58, H 4.51.

Embodiment 3

[0045] Example 3: Synthesis of gold complex 3

[0046] At 0℃, add n-BuLi (2.3mmol) n-hexane solution dropwise to o-C containing ortho carborane 2 B 10 H 12 (1.0mmol) in the ether solution, after the dropwise addition, continue to stir for 30 minutes, slowly rise to room temperature and continue the reaction for 30 minutes, and then add the halogenated phosphine ClP(4-NO 2 -C 6 H 4 ) 2 (3.0mmol), continue to react at room temperature for 2 hours, and then add AuCl (1.0mmol) to the reaction system at room temperature and continue to react for 4 hours. After the reaction is over, stand still and filter, drain the solvent under reduced pressure, and wash the crude product with ether , And drain to obtain the target product 3 (yield 81%), the reaction formula is:

[0047]

[0048] 1 H NMR(400MHz, CDCl 3 , 25°C): δ=7.82-7.75 (m, 8H), 7.64-7.57 (m, 8H). Elemental analysis theoretical value C 26 B 10 H 26 N 4 O 8 P 2 AuCl: C 33.76, H 2.83, N 6.06; experimental value: C 33.70, H 2.89, N 6.1...

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Abstract

The invention relates to a gold complex containing a diphosphine ortho-position carborane ligand as well as a preparation method and an application of the gold complex. The gold complex is prepared bythe following method: dropwise adding an n-BuLi solution into an ortho-carborane o-C2B10H12 solution, carrying out a stirring reaction, adding halogenated phosphine, continuously carrying out a reaction, adding aurous chloride AuCl into a reaction system, carrying out a reaction, and carrying out separation after the reaction is finished to obtain the gold complex containing the diphosphine ortho-carborane ligand. Compared with the prior art, the preparation method disclosed by the invention is simple and green, the monovalent gold complex can be obtained at high yield through one-pot reaction, the yield is high, the product separation is simple, and the product is insensitive to air and water and stable in property. The complex can efficiently catalyze the reaction of terminal alkyne andthioamide to synthesize the 2,4-disubstituted thiazole compound, has the advantages of low catalyst consumption, mild reaction conditions, high reaction rate, higher yield and wide substrate range, and has wide application prospects in industry.

Description

Technical field [0001] The invention relates to the field of complex synthesis, in particular to a gold complex containing a bisphosphine ortho carborane ligand, and a preparation method and application thereof. Background technique [0002] Thiazole compounds have broad application prospects in many fields such as organic synthesis, medicinal chemistry, biochemistry, and materials science, and have attracted more and more attention from researchers. Among them, 2,4-disubstituted thiazole structural units are widely present in many natural medicines or pharmaceutical intermediates, and have been proven to be the main effective ingredients in treatment (Adv. Synth. Catal. 2014, 356, 1229); people also seek Various methods are used to synthesize thiazole compounds. One is to functionalize the existing thiazole heterocycles, and the other is to use different linear precursors to synthesize thiazole heterocycles. The latter route is considered to be more potential and economical. Th...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F9/6596B01J31/24C07D277/22
CPCC07F9/6596C07D277/22B01J31/2409B01J2531/18B01J2231/324Y02P20/584
Inventor 姚子健付晨康梦浩王巍于泓倪轶凡
Owner SHANGHAI INST OF TECH
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