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1-(8-arylnaphthyl)phosphine ligand and preparation method thereof as well as phosphine-gold compound and application

A technology of phosphine ligands and complexes, applied in the field of organic synthesis, can solve problems such as harsh conditions, narrow substrate application range, and low yield

Inactive Publication Date: 2018-08-10
HUAZHONG NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The purpose of the present invention is to provide a 1-(8-arylnaphthyl)phosphine ligand complex preparation process, harsh conditions, low yield and narrow substrate application range defects in the prior art to provide a 1-(8-arylnaphthyl)phosphine ligand (8-aryl naphthyl) phosphine ligand and its preparation method as well as a phosphine-gold complex and the application of the phosphine-gold complex in the hydration reaction of 4-phenyl-3-butyn-2-one

Method used

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  • 1-(8-arylnaphthyl)phosphine ligand and preparation method thereof as well as phosphine-gold compound and application
  • 1-(8-arylnaphthyl)phosphine ligand and preparation method thereof as well as phosphine-gold compound and application
  • 1-(8-arylnaphthyl)phosphine ligand and preparation method thereof as well as phosphine-gold compound and application

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Embodiment approach

[0034] According to a preferred embodiment of the present invention, the substituted or unsubstituted heteroaryl is selected from R 1 and R' are each independently selected from methyl, methoxy or trifluoromethyl. Further preferably, R 1 is methoxy; R' is selected from methyl or trifluoromethyl.

[0035] According to a preferred embodiment of the present invention, the unsubstituted aryl is selected from phenyl,

[0036]

[0037] According to a preferred embodiment of the present invention, the ligand is represented by the following formula, wherein Ph represents phenyl,

[0038] Among them, R is selected from H, 3-methoxy, 4-methyl, 4-Cl, 4-COPh (Ph represents phenyl), 4-CF 3 , 4-9H-carbazole, 2 R" each independently selected from phenyl or cyclohexyl;

[0039]

[0040] R' is selected from methyl or trifluoromethyl;

[0041]

[0042] The second aspect of the present invention provides a method for preparing a 1-(8-arylnaphthyl)phosphine ligand, the method ...

Embodiment 1

[0079] This example is used to illustrate the preparation of 1-(8-phenylnaphthyl)diphenylphosphine.

[0080] 1-naphthyldiphenylphosphine (1mmol), bromobenzene (1mmol), [Rh(cod)Cl] 2 (0.025mmol), lithium tert-butoxide (3mmol) and toluene (5mL) were mixed in a pressure tube, heated to 110°C under nitrogen protection, and reacted at this temperature for 24 hours. After cooling to room temperature, the target product was separated by silica gel column chromatography (the volume ratio of petroleum ether to dichloromethane was 1:20) The yield was 82%. This product is analyzed, and the results are as follows:

[0081] 1 H NMR (400MHz, CDCl 3 ):δ7.91–7.88(m,2H,Ar),7.48(t,J=7.5Hz,1H,Ar),7.36–7.29(m,2H,Ar),7.22–7.15(m,8H,Ar) ,7.09–7.04(m,4H,Ar),6.94(t,J=7.2Hz,4H,Ar). 13 CNMR (101MHz, CDCl 3):δ143.5(d,J C-P =5.1Hz,Ar),141.3(d,J C-P =3.6Hz,Ar),139.4(d,J C-P =16.7Hz,Ar),137.2(s,Ar),135.5(s,Ar),135.2(d,J C-P =10.1Hz,Ar),134.9(d,J C-P =4.3Hz,Ar),133.7(d,J C-P =20.7Hz,Ar),130.8(...

Embodiment 2

[0083] This example is used to illustrate the preparation of 1-(8-p-methylphenylnaphthyl)diphenylphosphine.

[0084] 1-Naphthyldiphenylphosphine (1mmol), p-methylbromobenzene (1mmol), [Rh(cod)Cl] 2 (0.025mmol), lithium tert-butoxide (3mmol) and toluene (5mL) were mixed in a pressure tube, heated to 120°C under nitrogen protection, and reacted at this temperature for 24 hours. After cooling to room temperature, the target product was separated by silica gel column chromatography (the volume ratio of petroleum ether to dichloromethane was 1:20) The yield was 84%. This product is carried out nuclear magnetic resonance analysis, the result is as follows:

[0085] 1 H NMR (400MHz, CDCl 3 ): δ7.87(t, J=7.4Hz, 2H, Ar), 7.46(t, J=7.6Hz, 1H, Ar), 7.31(dd, J=15.4, 7.3Hz, 2H, Ar), 7.22– 7.15(m,7H,Ar),6.96–6.92(m,6H,Ar),6.84(d,J=7.7Hz,2H,Ar),2.33(s,3H,CH 3 ). 13 C NMR (101MHz, CDCl 3 ):δ141.4(d,J C-P =3.7Hz,Ar),140.4(d,J C-P =5.1Hz,Ar),139.6(s,Ar),139.4(s,Ar),137.3(s,Ar),136.5(...

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Abstract

The invention relates to the field of organic synthesis and discloses a 1-(8-arylnaphthyl)phosphine ligand and a preparation method thereof as well as a phosphine-gold compound and application. The ligand is shown as a formula (1), wherein each of two R'' is independently selected from phenyl and cyclohexyl and M is selected from substituted or unsubstituted heteroaryl and substituted or unsubstituted aryl; a heteroatom of the heteroaryl is a nitrogen atom; a substituent group of the heteroaryl is selected from at least one of methyl, methoxyl, trifluoromethyl, -Cl and -Br; the substituted aryl is shown as a formula (2). The 1-(8-arylnaphthyl)phosphine ligand can be directly prepared and the method is simple; the defect of a preparation method of the 1-(8-arylnaphthyl)phosphine ligand in the prior art that an applicable range of a substrate is narrow is overcome and the new 1-(8-arylnaphthyl)phosphine ligand is prepared; the yield of the method provided by the invention is high. The formula (1) and the formula (2) are shown in the description.

Description

technical field [0001] The invention relates to the field of organic synthesis, in particular to a 1-(8-arylnaphthyl)phosphine ligand, a preparation method thereof, a phosphine-gold complex and applications thereof. Background technique [0002] The unique chemical structure of 1-(8-arylnaphthyl)phosphine ligands makes them have great potential applications in electroluminescent materials and organic transformation reactions. [0003] At present, the method of synthesizing 1-(8-aryl naphthyl) phosphine that has been reported in the literature is to first synthesize 1-bromo-8-aryl naphthalene compound, then under the condition of strict anhydrous oxygen-free and low temperature and normal Butyllithium reaction, and then react with phosphine chloride to prepare 1-(8-aryl naphthyl) phosphine (Journal of the American Chemical Society, 2016,138,587-593; Chemistry-A European Journal, 2002,8,4633-4648 .). This method is not only complicated in operation, harsh in conditions, and ...

Claims

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Application Information

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IPC IPC(8): C07F9/50C07F9/58C07F9/60C07F9/6509C07F9/572B01J31/24C07C45/26C07C45/61C07C49/782
CPCB01J31/2447B01J2231/321B01J2531/18C07C45/26C07C45/61C07F9/5022C07F9/5045C07F9/5054C07F9/5728C07F9/60C07C49/782B01J2231/641C07F9/58C07F9/62C07F9/650952
Inventor 支志明余广鳌陈建袁佳罗雪
Owner HUAZHONG NORMAL UNIV
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