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A method for highly selective synthesis of 1,1,2-triiodoalkenes

A technology for triiodoalkenes and compounds, which is applied in the field of high-selectivity synthesis of 1,1,2-triiodoalkene compounds, can solve the problems of using metal catalysts, harsh reaction conditions, uncontrollable reactions, etc., and achieve mild reaction conditions, Ease of separation and purification, avoiding metal residue and toxicity

Active Publication Date: 2020-06-09
GUANGDONG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
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Problems solved by technology

[0003] The traditional methods for synthesizing iodoalkyne compounds are mainly metal catalysis, base catalysis and phase transfer catalysis, which often require the use of ultrasonic waves, Grignard reagents and lithium reagents for the synthesis reaction. The reaction conditions are harsh, the selectivity is low, and the reaction is uncontrollable. , need to use metal catalysts, pollute the environment and other problems

Method used

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  • A method for highly selective synthesis of 1,1,2-triiodoalkenes
  • A method for highly selective synthesis of 1,1,2-triiodoalkenes
  • A method for highly selective synthesis of 1,1,2-triiodoalkenes

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037]

[0038] Dissolve 38 μL (0.3 mmol) of p-methylphenylacetylene and 133 mg (0.36 mmol) of tetrabutylammonium iodide (TBAI) in 1 mL of acetonitrile, and add 96.6 mg (0.3 mmol) of iodobenzenediacetic acid to the In the reaction system, after reacting at room temperature for 3 hours, directly add 3 mL of water and 124.5 mg (0.75 mmol) of potassium iodide to the reaction system, and then add 193.2 mg (0.6 mmol) of iodobenzenediacetic acid into the reaction system in batches within 20 min , reacted at room temperature for 3 h, quenched the reaction with sodium thiosulfate, extracted three times with ethyl acetate, combined the organic phases and concentrated under reduced pressure to obtain the crude product 1. The crude product 1 was separated and purified by silica gel column chromatography (n-hexane 100%) to obtain a light-colored solid product 1 with a yield of 94%. With p-nitroacetophenone as the NMR internal standard, its NMR data are as follows:

[0039] 1 H NMR (4...

Embodiment 2

[0042]

[0043] Dissolve 38.9 μL (0.3 mmol) of 4-methoxyphenylacetylene and 133 mg (0.36 mmol) of tetrabutylammonium iodide in 1 mL of acetonitrile, and add 96.6 mg (0.3 mmol) of iodobenzenediacetic acid to the In the reaction system, after reacting at room temperature for 3 hours, directly add 3 mL of water and 124.5 mg (0.75 mmol) of potassium iodide to the reaction system, and then add 193.2 mg (0.6 mmol) of iodobenzenediacetic acid into the reaction system in batches within 20 min , reacted at room temperature for 3 h, quenched the reaction with sodium thiosulfate, extracted three times with ethyl acetate, combined the organic phases and concentrated under reduced pressure to obtain the crude product 2. The crude product 2 was separated and purified by silica gel column chromatography (n-hexane 100%) to obtain the light yellow solid product 2 with a yield of 90%. With p-nitroacetophenone as the NMR internal standard, its NMR data are as follows:

[0044] 1 H NMR (400M...

Embodiment 3

[0047]

[0048] Dissolve 33 μL (0.3 mmol) of phenylacetylene and 133 mg (0.36 mmol) of tetrabutylammonium iodide in 1 mL of acetonitrile, and add 96.6 mg (0.3 mmol) of iodobenzenediacetic acid into the reaction system in batches within 20 min. After reacting for 3 hours under the same conditions, directly add 3 mL of water and 124.5 mg (0.75 mmol) of potassium iodide to the reaction system, then add 193.2 mg (0.6 mmol) of iodobenzenediacetic acid into the reaction system in batches within 20 min, and react at room temperature 12h, and then add 124.5mg (0.75mmol) potassium iodide and 193.2mg (0.6mmol) iodobenzenediacetic acid to the reaction system, iodobenzenediacetic acid is added to the system in batches within 20min, react at room temperature for 6h and use The reaction was quenched with sodium thiosulfate, and then extracted three times with ethyl acetate. The organic phases were combined and concentrated under reduced pressure to obtain the crude product 3. The crude p...

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Abstract

The invention belongs to the technical field of synthetic chemistry and particularly relates to a method for synthesizing a 1, 1, 2-triiodo-olefin compound in a high-selectivity manner. The method is mild in reaction condition, controllable in reaction product, single in product, easy in product purification, high in chemical selectivity, simple in synthesizing step, safe, reliable, green, environmentally friendly, applicable to various terminal alkyne reaction substrates and suitable for industrial production, and the synthesizing yield of the method reaches up to 99%.

Description

technical field [0001] The invention belongs to the technical field of synthetic chemistry, and in particular relates to a method for synthesizing 1,1,2-triiodoalkene compounds with high selectivity. Background technique [0002] Iodoalkyne compounds are an important class of organic synthesis intermediates, which can be used to construct important molecular skeletons of fine chemicals, drug molecules and functional materials or as reaction precursors. It has important biological activity and has a wide range of applications in the fields of medicinal chemistry, applied chemistry and synthetic chemistry, and its synthesis and application are of great research value. Among them, the oxidative iodination reaction of alkynes is an important method for the synthesis of iodoalkyne compounds. [0003] The traditional methods for synthesizing iodoalkyne compounds are mainly metal catalysis, base catalysis and phase transfer catalysis, which often require the use of ultrasonic wave...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07B39/00C07C17/06C07C17/00C07C22/04C07C22/08C07C29/62C07C33/42C07C67/307C07C69/76C07C67/287C07C69/63C07C231/12C07C233/15C07C41/22C07C43/225
CPCC07B39/00C07C17/00C07C17/06C07C29/62C07C41/22C07C67/287C07C67/307C07C231/12C07C22/04C07C22/08C07C33/423C07C69/76C07C69/63C07C233/15C07C43/225
Inventor 刘艳黄达涯黄菊丸岡啓二
Owner GUANGDONG UNIV OF TECH
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