Synthetic method for furan coupling compound

A synthetic method and furan coupling technology, which is applied in the field of synthesis of furan coupling compounds, achieves the effects of high regioselectivity, wide substrate adaptability, and simple operation

Inactive Publication Date: 2014-06-25
NORTHWEST UNIV(CN)
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, as far as the inventors know, although furan is a very important and common heteroaromatic ring, this type of carbon-hydrogen bond activation strategy has not been applied to the coupling of furan compounds.

Method used

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  • Synthetic method for furan coupling compound
  • Synthetic method for furan coupling compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0015] IIa

[0016] In a 10mL single-necked flask was added Pd(OAc) 2 (22.4 mg, 10 mmol %), sealed and evacuated, replaced the air in the bottle with an oxygen balloon, and filled the flask with oxygen. Then, DMSO (1.5 mL) and TFA (75 μL, 1 mmol) were sequentially added to the flask via syringe under oxygen atmosphere, and the reaction mixture was stirred homogeneously at room temperature. Add 2-ethylfuran (105 μL, 1 mmol) to the well-stirred flask, react at room temperature for 24 h, and detect the reaction with a TLC plate until the reaction of the raw material is complete. A small amount of NaHCO was then added to the reaction mixture 3 Neutralize excess TFA, extract three times with ether, combine organic phases; wash with water, wash with saturated brine, wash with MgSO 4 Dry, concentrate under reduced pressure, and separate by column chromatography with n-hexane as the eluent to obtain self-coupling product IIa (76 mg, 80%).

[0017] IR (KBr) υ 3116, 2973, 2933, ...

Embodiment 2

[0019] IIb

[0020] In a 10mL single-necked flask was added Pd(OAc) 2 (22.4 mg, 10 mmol %), sealed and evacuated, replaced the air in the bottle with an oxygen balloon, and filled the flask with oxygen. Then, DMSO (1.5 mL), TFA (75 μL, 1 mmol) were sequentially added to the flask via syringe under an oxygen atmosphere, and the reaction mixture was stirred homogeneously at room temperature. Add 2-benzyloxymethylenefuran (188 mg, 1 mmol) to a well-stirred flask, react at 50°C for 24 hours, and detect the reaction with a TLC plate until the reaction of the raw materials is complete. A small amount of NaHCO was then added to the reaction mixture 3 Neutralize excess TFA, extract three times with ether, combine organic phases; wash with water, wash with saturated brine, wash with MgSO 4 Dry, concentrate under reduced pressure, and separate by column chromatography, using n-hexane / ethyl acetate as the eluent at 1:20, to obtain the self-coupling product IIb (159 mg, 85%).

[0...

Embodiment 3

[0023] IIc

[0024] In a 10mL single-necked flask was added Pd(OAc) 2 (22.4 mg, 10 mmol %), sealed and evacuated, replaced the air in the bottle with an oxygen balloon, and filled the flask with oxygen. Then, DMSO (1.5 mL), TFA (75 μL, 1 mmol) were sequentially added to the flask via syringe under an oxygen atmosphere, and the reaction mixture was stirred homogeneously at room temperature. Add ethyl 2-furan propionate (168 mg, 1 mmol) to the well-stirred flask, react at 50°C for 24 h, and detect the reaction with a TLC plate until the reaction of the raw materials is complete. A small amount of NaHCO was then added to the reaction mixture 3 Neutralize excess TFA, extract three times with ether, combine organic phases; wash with water, wash with saturated brine, wash with MgSO 4 Dry, concentrate under reduced pressure, and separate by column chromatography, using n-hexane / ethyl acetate as the eluent at 1:10, to obtain the self-coupling product IIc (136 mg, 81%).

[0025]...

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Abstract

The invention discloses a synthetic method for a furan coupling compound. The synthetic method comprises the following steps: by taking substituted furan as a starting raw material, palladium trifluoroacetate or palladium acetate as a catalyst and oxygen as an oxidant, carrying out one-step synthesis in an organic solvent to obtain a substituted furan coupling product. According to the method, furan coupling directly oxidized by a C-H bond can be realized, the method is simple to operate compared with the traditional method, a substrate application range is wider, the reaction efficiency is higher, and the method is environmentally-friendly, high in yield and high in atom utilization rate.

Description

technical field [0001] The invention relates to a synthesis method of a furan coupling compound, which belongs to the technical field of organic synthesis. Background technique [0002] Oligomeric furan compounds play important and widespread roles in nature, medicine, and functional materials. Therefore, many organic chemists try to find effective synthetic methods to synthesize such compounds. The traditional synthesis method is through the reaction of furan halides with organometallic reagents of furan, boronic acid reagents of furan, and other electron-rich furan reagents; or through direct self-coupling of two furan organometallic reagents or two furan halides. These methods need to prepare furan halides or metal reagents in advance, so the steps are cumbersome; and the high reactivity of organometallic reagents is easy to react with water and oxygen, so these reactions generally need to be carried out in an anhydrous and oxygen-free atmosphere. Harsh, the reaction re...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D307/36C07D307/42C07D307/54
CPCC07D307/36C07D307/42C07D307/54
Inventor 王永强李娜娜
Owner NORTHWEST UNIV(CN)
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