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Method for synthesizing alpha-beta unsaturated acetyenic ketone compounds by carbonylation

A chemical synthesis and unsaturated technology, applied in the field of α-β unsaturated alkynone compounds, can solve the problems of the homogeneous catalyst product and catalyst being difficult to separate, the toxicity of phosphine compounds, etc., and achieves low cost, high reaction activity and mild reaction conditions. Effect

Inactive Publication Date: 2012-07-04
LANZHOU INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

But these catalyst systems exist: 1) the toxicity of phosphine compound; 2) the inherent product of homogeneous catalyst and the defect that catalyst is difficult to separate

Method used

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  • Method for synthesizing alpha-beta unsaturated acetyenic ketone compounds by carbonylation

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] 5%Pd / C: 10mg, Et 3 N: 7.2mmol, iodobenzene: 2.5mmol, phenylacetylene: 3mmol, 4ml toluene, carbon monoxide pressure 2.0MPa, reaction at 130°C for 4h to obtain 1,3-Diphenyl-2-propynone. The conversion rate of iodobenzene is 96%, and the selectivity of 1,3-Diphenyl-2-propynone is greater than 99%.

Embodiment 2

[0025] Same as Example 1, without adding alkali, no 1,3-Diphenyl-2-propynone was obtained.

Embodiment 3

[0027] Same as Example 1, the base used is pyridine (7.2 mmol) to obtain 1,3-Diphenyl-2-propynone. The conversion rate of iodobenzene is 28%, and the selectivity of 1,3-Diphenyl-2-propynone is greater than 99%.

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Abstract

The invention discloses a method for synthesizing an alpha-beta unsaturated acetyenic ketone compound through carbonylation. The method is to take iodo arene, a terminal acetylene compound and carbon monoxide as reactants and activated carbon loaded palladium as a catalyst, to control the reaction temperature to be between 80 and 140 DEG C and the pressure of the carbon monoxide to be between 0.5and 3.0 MPa in the presence of a catalyst accelerator and a reaction solvent, and to react for 1 to 4 hours to obtain products. The method can realize separation of the catalyst and the products after the reaction is over, and can reuse the catalyst and maintain the activity of the catalyst unchanged; and the selectivity is more than 99 percent, and the conversion rate is more than 90 percent. The method has good industrial application prospect.

Description

technical field [0001] The invention relates to a method for synthesizing α-β unsaturated acetylenic ketone compounds through Carbonylative Sonogashira Coupling (Carbonylative Sonogashira Coupling) of heterogeneous palladium-catalyzed iodobenzene compounds and terminal alkynes under mild conditions. Background technique [0002] α-β unsaturated alkyne ketones are extremely important organic intermediates, widely used in the synthesis of heterocyclic compounds, bioactive macromolecules (such as: vitamins, nucleosides, amino acids, etc.), natural products, drugs, etc. (reference : C. Chowdhury, N.G. Kundu, Tetrahedron 1999, 55, 7011 and references therein.). The traditional method (reference: L.Delaude, A.M.Masdeu, H.Alper, Synthesis 1994, 1149.) of synthesizing α-β unsaturated alkyne ketone mainly contains 1) the coupling reaction of the alkynyl compound of acid chloride and metal; 2) tin Or the coupling reaction of silicon alkynyl compounds with organic halides in the prese...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C49/213C07C45/50
Inventor 陈静刘建华夏春谷
Owner LANZHOU INST OF CHEM PHYSICS CHINESE ACAD OF SCI