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Method for converting Z-type alpha, beta-diaryl olefin compound into E-type alpha, beta-diaryl olefin compound

A technology for diaryl olefins and compounds, which is used in the preparation of chemicals, the conversion of α, β-diaryl olefin compounds from Z formula to E formula, which can solve the problem of large catalyst dosage, unstable conversion rate and broad substrate spectrum. problems such as poor performance, to achieve the effect of less catalyst dosage, low production cost and high conversion rate

Active Publication Date: 2022-06-28
VALIANT CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] In summary, the current catalytic isomerization method mainly has the following technical problems: 1) the amount of catalyst is large (more than 5% mol), and some catalytic systems need to be irradiated with light; 2) additional equivalent-level additives are required, and the substrate has a broad spectrum 3) It is easy to produce ethylenic bond migration impurities, and the conversion rate is unstable

Method used

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  • Method for converting Z-type alpha, beta-diaryl olefin compound into E-type alpha, beta-diaryl olefin compound
  • Method for converting Z-type alpha, beta-diaryl olefin compound into E-type alpha, beta-diaryl olefin compound
  • Method for converting Z-type alpha, beta-diaryl olefin compound into E-type alpha, beta-diaryl olefin compound

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] n=2, R 1 is n-propyl, R 2 , R 4 is a hydrogen atom, R 3 When it is a chlorine atom;

[0034] Preparation of compound II:

[0035]

[0036] Under nitrogen protection, 166g (0.5mol) of compound I (compound I is the reaction substrate, wherein the composition GC ratio of compound I is E:Z=13:87), 498g of ethanol (solvent) were successively added to the clean and dry reaction flask. The feeding amount is based on the amount of compound I, the same below), 0.05g (0.00022mol) Pd(OAc) 2 , 0.19g (0.00044mol) CXA·HBr (the palladium catalyst and the phosphine ligand charging amount are converted according to the GC purity of Z formula in compound I, the same below), mechanically stir until the system is uniform, and it is a yellow and clear system.

[0037] Feeding is finished, be warmed up to 78 ℃ of temperature in the reaction flask, reflux insulation reaction for 8 hours, complete the reaction, be cooled to 50 ℃, cross 17g diatomaceous earth, filter, and dehydrate the ...

Embodiment 2

[0039] With embodiment 1, wherein different step is to use the PdCl of 0.04g 2 Instead of 0.05g (0.00022mol) Pd(OAc) 2 , the reflux holding time is 12h, and finally 149g of compound II is obtained, the yield is 90%, and the GC purity is 99.8%.

Embodiment 3

[0041] With embodiment 1, wherein different step is to use the PPh of 0.12g 3 Instead of 0.19 g (0.00044 mol) CXA·HBr, the reflux holding time was 10 h, and finally 141 g of compound II was obtained, the yield was 90%, and the GC purity was 99.8%.

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Abstract

The invention relates to a method for converting an alpha, beta-diaryl olefin compound from a formula Z into a formula E. The method is characterized by comprising the following steps: converting the alpha, beta-diaryl olefin compound from the formula Z into the alpha, beta-diaryl olefin compound from the formula E under the protection of inert gas and the action of a palladium-phosphine complex catalyst; the palladium-phosphine complex catalyst comprises a palladium catalyst and a phosphine ligand, the palladium catalyst is at least one of Pd (OAc) 2, PdCl2 and Pd (PPh3) 4, and the phosphine ligand is at least one of CXA.HBr, PPh3 and Xphos. According to the method for converting the alpha, beta-diaryl olefin compound from the Z formula to the E formula, an adopted catalyst system is simple and easy to obtain, the dosage of the catalyst is only five-ten-thousandth equivalent, meanwhile, a reaction substrate is wide in application range and high in conversion rate, the product purity is 99% or above, the product yield is 90% or above, and the method is suitable for large-scale industrial production.

Description

technical field [0001] The invention relates to a method for converting an α,β-diaryl olefin compound from a Z formula to an E formula, and belongs to the technical field of chemical preparation methods. Background technique [0002] α, β-Diarylolefin compounds are important intermediates in the fields of liquid crystal and medicine, and the synthesis of such compounds has important application value. These compounds are mainly synthesized by elimination reaction, wittig reaction and alkyne reduction reaction, but the products generally exist in the form of Z / E configuration mixtures, however, the Z / E configuration of the same alkene has great advantages in physical properties, reactivity, biological There are large differences in activity and photoelectric performance. The purification process of the single-configuration product is cumbersome and the yield is low. High-purity single-configuration products often need to be obtained through transformation reactions. At pres...

Claims

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Application Information

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IPC IPC(8): C07C17/358C07C25/24C07C5/22C07C15/52
CPCC07C17/358C07C5/2293C07B2200/09C07C2531/24C07C25/24C07C15/52
Inventor 李东君王磊孙戈亮李忠鹏仪登京
Owner VALIANT CO LTD
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