Phosphine imide ligand (E)-(2-(diphenyl phosphino) benzylidene) hydrazine as well as synthetic method and application of phosphine imide ligand (E)-(2-(diphenyl phosphino) benzylidene) hydrazine

A technology of diphenylphosphino and benzylidene, applied in the field of catalyst ligand preparation, can solve the problems of unsatisfactory results, unsatisfactory ligand activity, toxic palladium and the like, and achieves short reaction time , The effect of convenient post-processing and high reactivity

Inactive Publication Date: 2012-07-25
NANKAI UNIV +1
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Problems solved by technology

Buchwald et al. reported the application of diarylphosphine ligands in asymmetric reactions, see: Angew.Chem., Int.Ed.2003, 42, 5993, but this ligand is not effective in catalyzing the halogenation of terminal alk...

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  • Phosphine imide ligand (E)-(2-(diphenyl phosphino) benzylidene) hydrazine as well as synthetic method and application of phosphine imide ligand (E)-(2-(diphenyl phosphino) benzylidene) hydrazine
  • Phosphine imide ligand (E)-(2-(diphenyl phosphino) benzylidene) hydrazine as well as synthetic method and application of phosphine imide ligand (E)-(2-(diphenyl phosphino) benzylidene) hydrazine
  • Phosphine imide ligand (E)-(2-(diphenyl phosphino) benzylidene) hydrazine as well as synthetic method and application of phosphine imide ligand (E)-(2-(diphenyl phosphino) benzylidene) hydrazine

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Embodiment

[0025] A kind of synthetic method of described phosphine imide ligand (E)-(2-(diphenylphosphino)benzylidene)hydrazine, the steps are as follows:

[0026] (1) Preparation of intermediate 2-diphenylphosphinobenzaldehyde

[0027] 1) Add 25.0g (0.131mol) o-bromobenzaldehyde, 12.5g (0.201mol) ethylene glycol and 0.11g (0.58mmol) p-toluenesulfonic acid to 150ml toluene under the protection of argon. Reflux reaction for 25 hours, when no more water is produced in the water separator, stop heating, concentrate, wash with sodium bicarbonate and saturated brine, extract with dichloromethane, dry over anhydrous magnesium sulfate, spin dry, and distill under reduced pressure to obtain 2-(2-bromophenyl)-1,3-dioxolane 27.86g, yield 93%;

[0028] 2) Under argon protection, 27.8g (0.121mol) 2-(2-bromophenyl)-1,3-dioxolane, 2.96g (0.122mol) magnesium chips and 0.04g (0.157mmol) Add iodine to 200ml tetrahydrofuran, and reflux at 50°C for 2 hours to obtain 30.7g Grignard reagent;

[0029] 3) ...

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Abstract

The invention relates to phosphine imide ligand (E)-(2-(diphenyl phosphino) benzylidene) hydrazine, which belongs to a diphosphine ligand containing imide groups and contains two atoms coordinated with metal ions. A synthetic method is characterized in that the final target is prepared through preparing an intermediate of 2-diphenylphosphine benzaldehyde; and phosphine imide ligand and cuprous salt form a catalyst system, and the catalyst system is used for cross-coupling catalytic reaction between terminal alkyne and sp2 type carbon halide for preparing substituted diphenylacetylene. The phosphine imide ligand (E)-(2-(diphenyl phosphino) benzylidene) hydrazine has the advantages that the catalyst system has high reaction reactivity on aryl iodide substrates and also has a certain activity on aryl bromide, the applicable substrate range is wide, and in addition, self-coupling products can be perfectly controlled not to be generated; the synthetic method is simple, and the post treatment is convenient; expensive and toxic palladium is not used in the catalysis, and cheap, economic and clean copper which is easy to obtain is adopted; and organic amine is not used as an alkaline solvent, in addition, the reaction time is short, the catalyst consumption is low, and good application prospects are realized in industrial production.

Description

technical field [0001] The present invention relates to the preparation of the catalyst ligand that is used for cross-coupling reaction, especially a kind of synthesis method of phosphine imide ligand (E)-(2-(diphenylphosphino)benzylidene)hydrazine and its applications in catalysis. Background technique [0002] Phosphine imide ligands are an important class of P-N ligands, which have good applications in many metal-catalyzed asymmetric reactions. Buchwald et al. reported the application of diarylphosphine ligands in asymmetric reactions, see: Angew.Chem., Int.Ed.2003, 42, 5993, but this ligand is not effective in catalyzing the halogenation of terminal alkynes with sp2-type carbons The results in the cross-coupling reaction between compounds are not very satisfactory, especially the expensive and toxic palladium is used in the catalysis, and the activity of the ligand is not very good. Our research found that the cross-coupling reaction between the terminal alkyne and the...

Claims

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Application Information

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IPC IPC(8): C07F9/50B01J31/24C07B37/00C07C2/86C07C15/54C07C17/266C07C25/24C07C41/30C07C43/215C07C201/12C07C205/06C07C209/68C07C211/45
Inventor 徐凤波朱佳芳罗山峰许荣花孔晓菲敖丽华金艳娟
Owner NANKAI UNIV
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