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Alkyne ketone-promoted method for CuI-catalyzed sonogashira coupling reactions

A technology of coupling reaction and acetylene ketone is applied in the field of acetylene ketone to promote CuI catalyzed Sonogashira coupling reaction.

Inactive Publication Date: 2018-03-06
SHAANXI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The catalytic efficiency of these σ electron donor ligands leads to a large amount of copper catalyst (5-20mol%)

Method used

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  • Alkyne ketone-promoted method for CuI-catalyzed sonogashira coupling reactions
  • Alkyne ketone-promoted method for CuI-catalyzed sonogashira coupling reactions

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0016] 0.11g (0.5mmol) 4-methoxyiodobenzene, 0.0009g (0.005mmol) CuI, 0.0045g (0.02mmol) 1-(4-methoxyphenyl)-3-phenyl-2-ethynyl -1-ketone and 0.0689g (0.5mmol) K 2 CO 3 Put it into a Shrek tube, add 3mL DMF under nitrogen protection, then add 66μL (0.6mmol) phenylacetylene, react the reaction system at 120°C for 12 hours, naturally cool to room temperature, extract with ethyl acetate, and the organic phase is subjected to column chromatography Separation (gradient elution with a mixture of dichloromethane and petroleum ether at a volume ratio of 0:1, 1:100, 1:50, and 1:10) gave light yellow solid 1-methoxy-4-(benzene Ethynyl)benzene, the yield was 80%.

Embodiment 2

[0018] In Example 1, the 1-(4-methoxyphenyl)-3-phenyl-2-ethynyl-1-one was used with equimolar 1-(1-naphthyl)-3-phenyl- 2-ethynyl-1-one was replaced, and the other steps were the same as in Example 1 to obtain 1-methoxy-4-(phenylethynyl)benzene as a light yellow solid with a yield of 55%.

Embodiment 3

[0020] In Example 1, the 1-(4-methoxyphenyl)-3-phenyl-2-ethynyl-1-ketone was used with equimolar 1-(4-methoxyphenyl)-3- (2-thienyl)-2-ethynyl-1-ketone replacement, other steps are the same as in Example 1, to obtain light yellow solid 1-methoxy-4-(phenylethynyl)benzene, and its yield is 79% .

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Abstract

The invention discloses an acetyenic-ketone-promoted CuI-catalyzed method for conducting a Sonogashira coupled reaction. The method includes the steps that acetyenic ketone rich in pi-sigma electrons serves as a ligand, CuI serves as a catalyst, a Sonogashira cross coupling reaction between aryl halide and terminal alkyne is catalyzed, and arylethynylene compounds are synthesized. The method is simple in operation and mild in condition, a substrate is good in applicability, a toxic phosphine ligand is avoided, CuI consumption is obviously reduced, and the method can be widely applied to synthesis of the arylethynylene compounds.

Description

technical field [0001] The invention belongs to the technical field of methods for synthesizing alkyne compounds through Sonogashira coupling, and in particular relates to a method for synthesizing alkyne compounds using acetylenic ketone compounds as ligands and transition metal compounds as catalysts. Background technique [0002] Alkyne compounds have a variety of physiological activities, and are important small molecules to construct heterocyclic structures. Recently, they have attracted the attention of researchers. It has a wide range of applications in the fields of chemical synthesis, copolymers, and materials. [0003] Regarding the synthesis of alkyne compounds, the earliest studies were reported by Cassar and Heck in 1975. Heck's method is based on the known palladium-catalyzed Mizoroki-Heck reaction for olefin arylation or alkenylation and involves the use of a phosphine-palladium compound as catalyst, triethylamine or piperidine as base and solvent. Cassar's ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07B37/00C07C2/86C07C15/54C07C41/30C07C43/215C07C45/68C07C49/796C07C67/343C07C69/76C07C201/12C07C205/06C07C17/266C07C22/08C07C43/225C07D333/16B01J31/22
CPCB01J31/2286B01J2231/4266B01J2531/02B01J2531/16C07B37/00C07C2/861C07C17/266C07C41/30C07C45/68C07C67/343C07C201/12C07D333/16C07C15/54C07C43/215C07C49/796C07C69/76C07C205/06C07C22/08C07C43/225
Inventor 张伟强王贤谢遵园高子伟张国防杨金斗魏贞王振华王秀
Owner SHAANXI NORMAL UNIV