A Novel Alkylated Monophosphine Ligand and Its Simple Preparation Method

A technology of alkylation and ligands, applied in the field of new monophosphine ligands and their synthesis, new alkylated monophosphine ligands and their simple preparation, can solve the problem of single type of alkylation, complicated preparation process, and difficult operation process Complexity and other issues, to achieve the effect of reducing production costs, simple synthesis steps, and simple operation process

Active Publication Date: 2021-03-16
HUBEI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0012] In view of this, the application provides a novel alkylated monophosphine ligand and a simple preparation method thereof, which solves the problem of monophosphine ligands in the prior art with a single type of alkylation, complex preparation process, high production cost, and difficult operation. Problems such as complex process and low yield, and the development of a variety of new alkylated monophosphine ligands

Method used

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  • A Novel Alkylated Monophosphine Ligand and Its Simple Preparation Method
  • A Novel Alkylated Monophosphine Ligand and Its Simple Preparation Method
  • A Novel Alkylated Monophosphine Ligand and Its Simple Preparation Method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] The novel alkylated monophosphine ligand III-1{3-(2'-(diphenylphosphino)-[1,1'-biphenyl]-2-yl) ethyl propionate} of this example, The synthetic route is as follows:

[0036]

[0037] The above-mentioned novel alkylated monophosphine ligand III-1 is prepared by the following method, including the following steps:

[0038] Add 101.4 mg (0.3 mmol) 2-diphenylphosphine-biphenyl (compound I-1), 82.5 μL ethyl acrylate (compound II-1, 0.76 mmol), 9.3 mg p-cymene dichloride to the reaction kettle Ruthenium dimer, 15.8mg N-Boc-glycine, 5.3mg tris(4-methoxyphenyl) phosphine, 58.8mg potassium acetate and 1.5mL n-hexane, stirred and mixed evenly, then passed argon into the reaction system, The reaction was controlled in an argon atmosphere at 120° C. for 24 hours, then cooled to room temperature, filtered with diatomaceous earth, vacuum distilled, and separated by column chromatography to obtain 93.8 mg of the target product with a yield of 71%.

[0039] The target product test r...

Embodiment 2

[0048] The new alkylated monophosphine ligand III-2{3-(2'-(diphenylphosphino)-[1,1'-biphenyl]-2-yl) tert-butyl propanoate }, the synthetic route is as follows:

[0049]

[0050] The above-mentioned novel alkylated monophosphine ligand III-2 is prepared by the following method, including the following steps:

[0051] Add 101.4 mg (0.3 mmol) 2-diphenylphosphine-biphenyl (compound I-2), 141 μL tert-butyl acrylate (compound II-2), 9.3 mg p-cymene dichloride ruthenium dichloride to the reaction kettle Polymer, 15.8mg N-Boc-glycine, 5.3mg tris(4-methoxyphenyl) phosphine, 58.8mg potassium acetate and 1.5mL n-hexane, stirred and mixed evenly, and passed argon gas into the reaction system to control the reaction at After reacting at 120° C. for 24 h in an argon atmosphere, it was cooled to room temperature, filtered with diatomaceous earth, vacuum distilled, and separated by column chromatography to obtain 101 mg of the target product with a yield of 72%.

[0052] The target produc...

Embodiment 3

[0058] The novel alkylated monophosphine ligand III-3{3-(2'-(diphenylphosphoryl)-[1,2'-methoxybiphenyl]-2-yl)propane of this example Acid ethyl ester}, the synthetic route is as follows:

[0059]

[0060] The above-mentioned novel alkylated monophosphine ligand III-3 is prepared by the following method, including the following steps:

[0061] Add 110.9 mg (0.3 mmol) 2-methoxy-2-diphenylphosphine-biphenyl (compound I-3), 82.5 μL ethyl acrylate, 9.3 mg p-cymene dichloride ruthenium dichloride to the reaction kettle Polymer, 15.8mg N-Boc-glycine, 5.3mg tris(4-methoxyphenyl) phosphine, 58.8mg potassium acetate and 1.5mL n-hexane, stirred and mixed evenly, and passed argon gas into the reaction system to control the reaction at The reaction was carried out at 160° C. for 24 h in an argon atmosphere, cooled to room temperature, filtered with diatomaceous earth, vacuum distilled, and separated by column chromatography to obtain 115 mg of the target product with a yield of 71%.

...

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Abstract

The invention relates to a novel alkylated monophosphine ligand and a simple production method thereof, and belongs to the technical field of organic chemistry. The novel alkylated monophosphine ligand is produced by using a structural formula I compound and a structural formula II compound as raw materials, carrying out constant-temperature reaction for 20-30 h in the presence of a ruthenium catalyst, a ligand, alkali, an additive and an organic solvent in an inert atmosphere at 50-180 DEG C, finally cooling a product to room temperature, and conducting suction filtration, reduced pressure distillation and column chromatography isolation on the obtained product. The production method has a simple synthesis step, can be implemented only by adopting one step, and has the advantages that theraw materials are easy to obtain, technology operation is simple and convenient, the production method is efficient and fast, the production cost is reduced, the requirements of equipment are reduced, and the like, moreover, the product yield is high, and industrial large-scale production is easy to achieve.

Description

technical field [0001] The invention belongs to the technical field of organic chemistry and relates to a novel monophosphine ligand and a synthesis method thereof. More specifically, the invention relates to a novel alkylated monophosphine ligand and a simple preparation method thereof. Background technique [0002] Monophosphine ligands are widely used in transition metal-catalyzed coupling reactions, which play a key role in improving catalyst activity, reaction yield, regioselectivity and enantioselectivity. [0003] With the rapid development of transition metal-catalyzed coupling reactions, the development of novel alkylated monophosphine ligands has attracted more and more attention. [0004] The synthesis of novel alkylated monophosphine ligands has been reported in some literatures, mainly including highly active metal lithium reagents and metal catalysis such as rhodium and ruthenium, thereby introducing the most critical alkyl substituents. The synthesis method ha...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F9/50C07F9/655C07F9/572C07F9/6533
Inventor 刘悦进王良能李佳威曾明华李明唐潘婷
Owner HUBEI UNIV
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