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Method for preparing 1-naphthol phosphine oxide ligand

A naphthol-based phosphine and ligand technology, which is applied in the field of preparation of 1-naphthol-based phosphine oxygen ligands, can solve the problems that affect the development and application of ligands, is difficult to handle, has a single structure, etc., and achieves high yield and low cost. The effect of good adaptability and simple steps

Active Publication Date: 2019-08-30
FOSHAN UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the traditional methods for synthesizing 1-naphthylphosphine oxygen ligands have problems such as harsh conditions, difficult handling, and single structure, which greatly affect the development and application of such ligands.

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0011] Preparation of (2-phenyl-4-hydroxynaphthyl) diphenylphosphine oxide, the structural formula is:

[0012] In a pre-dried 25mL Schlenk tube equipped with magnetons, add phenylethynyl diphenylphosphine (0.1mmol), benzoylthioylide compound (0.18mmol), 6.66mg (0.008mmol, 8%) [RhCp *(CH 3 EN) 3 ](SbF 6 ) 2 , 5.5mg (0.03mmol, 30%) zinc acetate, then add 4.0mL dry DCE, place the reaction tube in a preheated 80°C oil bath, react in a nitrogen atmosphere for 16h, remove the reaction from the heat source, then Add dichloromethane, transfer to a round bottom flask, remove the solvent with a rotary evaporator, ethyl acetate / dichloromethane=1:3, pass through a silica gel column to obtain 38.6 mg of the target product, and the yield is 92%.

[0013] The compound is characterized as follows:

[0014] 1 H NMR (400MHz, DMSO): δ10.48(s, 1H), 8.24(d, J=8.2Hz, 1H), 7.60–7.54(m, 1H), 7.54–7.37(m, 11H), 7.20–7.12 (m,2H),7.04(t,J=7.6Hz,2H),6.99–6.89(m,3H);

[0015] 13 C NMR (101MHz,...

Embodiment 2

[0019] Preparation of (7-methyl-2-phenyl-4-hydroxynaphthyl) diphenylphosphine, the structural formula is:

[0020] In a pre-dried 25mL Schlenk tube equipped with a magnet, add phenylethynyl diphenylphosphine (0.1mmol), 4-methylbenzoylthioylide compound (0.18mmol), 6.66mg (0.008mmol, 8 %)[RhCp*(CH 3 EN) 3 ](SbF 6 ) 2 , 5.5mg (0.03mmol, 30%) zinc acetate, then add 4.0mL dry DCE, place the reaction tube in a preheated 80°C oil bath, react in a nitrogen atmosphere for 16h, remove the reaction from the heat source, then Add dichloromethane, transfer to a round bottom flask, remove the solvent with a rotary evaporator, ethyl acetate / dichloromethane=1:3, pass through a silica gel column to obtain 32.0 mg of the target product, with a yield of 74%.

[0021] The compound is characterized as follows:

[0022] 1 H NMR (400MHz, DMSO): δ10.42(s, 1H), 8.14(d, J=8.5Hz, 1H), 7.53–7.46(m, 6H), 7.39(td, J=8.1, 2.1Hz, 5H ),7.15(dd,J=10.5,4.3Hz,1H),7.03(t,J=7.6Hz,2H),6.94(s,1H),6.89(dd,J...

Embodiment 3

[0027] Preparation of (2-phenyl-4-hydroxyl-7-methoxynaphthyl) diphenylphosphine, the structural formula is:

[0028] In a pre-dried 25mL Schlenk tube equipped with a magnet, add phenylethynyl diphenylphosphine (0.1mmol), 4-methoxybenzoylthioylide compound (0.18mmol), 6.66mg (0.008mmol, 8%)[RhCp*(CH 3 EN) 3 ](SbF 6 ) 2 , 5.5mg (0.03mmol, 30%) zinc acetate, then add 4.0mL dry DCE, place the reaction tube in a preheated 80°C oil bath, react in a nitrogen atmosphere for 16h, remove the reaction from the heat source, then Add dichloromethane, transfer to a round bottom flask, remove the solvent with a rotary evaporator, ethyl acetate / dichloromethane=1:3, pass through a silica gel column to obtain 35.3 mg of the target product, with a yield of 78%.

[0029] The compound is characterized as follows:

[0030] 1 H NMR (400MHz, DMSO): δ10.39(s, 1H), 8.16(d, J=9.2Hz, 1H), 7.50(dd, J=10.7, 7.8Hz, 6H), 7.43–7.37(m, 4H ),7.25(dd,J=9.2,2.5Hz,1H),7.15(t,J=7.4Hz,1H),7.05(t,J=7.5Hz,2H)...

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Abstract

The invention discloses a method for preparing a 1-naphthol phosphine oxide ligand. The method comprises the following steps: uniformly mixing a sulfur ylide compound, a phenylethyny phosphine oxide derivative, a catalyst, a Lewis acid and an organic solvent, and reacting in nitrogen at a temperature of 60-100 DEG C for 6-16 hours, thereby obtaining the finished 1-naphthol phosphine oxide ligand of a structural formula as shown in the specification. According to the method disclosed by the invention, the 1-naphthol phosphine oxide ligand that is difficultly prepared in the conventional synthetic method can be obtained, the step of the method is simple, and the 1-naphthol phosphine oxide ligand can be constructed by one step only. Moreover, the method is mild in reaction condition, excellent in substrate adaptability and high in yield, and can synthesize the 1-naphthol phosphine oxide ligand of multiple different substituent groups.

Description

technical field [0001] The invention relates to the field of organic synthesis, in particular to a preparation method of 1-naphthylphosphine oxygen ligand. Background technique [0002] Oxides of organic phosphine, because the phosphoryl oxygen atom has a lone pair of electrons, it has a strong coordination ability and can form complexes with various metal ions. Phosphine oxides can also be used as ligands in various metal-catalyzed homogeneously catalyzed reactions. It is widely used in the production process of chemical industry. For example: transition metal ions can be extracted from aqueous solution, and the excitation wavelength of metal ions can be adjusted in organic light-emitting materials. In addition, chiral phosphine oxide ligands combined with metals can be used as chiral Lewis acid catalysts in the field of asymmetric synthesis. However, the traditional methods for synthesizing 1-naphthylphosphine oxygen ligands have problems such as harsh conditions, diffic...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F9/53
CPCC07F9/5325
Inventor 谢吴成张滢简心仪林钦洪林佳豪
Owner FOSHAN UNIVERSITY
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