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Method for synthesizing 1, 2-diiodo-olefin compound in high-selectivity manner

A diiodoalkene, high-selectivity technology, applied in the field of synthetic chemistry, can solve the problems of using metal catalysts, harsh reaction conditions, and uncontrollable reactions, and achieve the effect of single product, mild reaction conditions, and easy separation and purification

Active Publication Date: 2017-06-13
GUANGDONG UNIV OF TECH
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  • 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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  • Method for synthesizing 1, 2-diiodo-olefin compound in high-selectivity manner
  • Method for synthesizing 1, 2-diiodo-olefin compound in high-selectivity manner
  • Method for synthesizing 1, 2-diiodo-olefin compound in high-selectivity manner

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Experimental program
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Effect test

Embodiment 1

[0034]

[0035] Dissolve 38 μL (0.3 mmol) of p-methylphenylacetylene in 3 mL of acetonitrile, then add 3 mL of water and 124.5 mg (0.75 mmol) of potassium iodide, then add 96.6 mg (0.3 mmol) of iodobenzenediacetic acid to the reaction in batches within 30 min In the system, react at room temperature for 24 h, and then extract three times with ethyl acetate, combine the organic phases and concentrate 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 111.9 mg of yellow liquid product 1 with a yield of 98%, and its NMR data were as follows:

[0036] 1 H NMR (400MHz, CDCl 3 , ppm): δ=7.26(d, J=8.0Hz, 2H), 7.22(s, 1H), 7.16(d, J=8.0Hz, 2H), 2.36(s, 3H);

[0037] 13 C NMR (100MHz, CDCl 3 , ppm): δ=140.2, 139.0, 129.1, 128.5, 96.6, 80.1, 21.4.

Embodiment 2

[0039]

[0040] Dissolve 33 μL (0.3 mmol) of phenylacetylene in 1 mL of acetonitrile, then add 3 mL of water and 124.5 mg (0.75 mmol) of potassium iodide, then add 96.6 mg (0.3 mmol) of iodobenzenediacetic acid to the reaction system in batches within 30 min, React at room temperature for 24 h, then extract three times with ethyl acetate, combine the organic phases and concentrate 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 104.5 mg of white solid product 2 with a yield of 94%. The NMR data are as follows:

[0041] 1 H NMR (400MHz, CDCl 3 ,ppm):δ=7.26-7.36(m,5H),7.24(s,1H);

[0042] 13 C NMR (100MHz, CDCl 3 , ppm): δ=143.1, 129.0, 128.5, 128.4, 96.2, 80.8.

Embodiment 3

[0044]

[0045] Dissolve 34.4 μL (0.3 mmol) of 4-fluorophenylacetylene in 1 mL of acetonitrile, then add 3 mL of water and 124.5 mg (0.75 mmol) of potassium iodide, and then add 193.3 mg (0.6 mmol) of iodobenzenediacetic acid to the In the reaction system, react at room temperature for 12 h, then extract three times with ethyl acetate, combine the organic phases and concentrate under reduced pressure to obtain the crude product 3. The crude product 3 was separated and purified by silica gel column chromatography (n-hexane 100%) to obtain 108.8 mg of yellow liquid product 3 with a yield of 97%. The NMR data are as follows:

[0046] 1 H NMR (400MHz, CDCl 3 , ppm): δ=7.33-7.36(m, 2H), 7.26(s, 1H), 7.06(t, J=8.8Hz);

[0047] 13 C NMR (100MHz, CDCl 3 , ppm): δ=162.5 (d, J=248Hz), 139.1 (d, J=3.4Hz), 130.6 (d, J=8.5Hz), 115.6 (d, J=21.9Hz), 94.9, 81.5.

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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, 2-diiodo-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 1,2-diiodoalkene 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 waves, ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07B39/00C07C17/02C07C17/00C07C22/04C07C22/08C07C29/62C07C33/42C07C67/307C07C69/76C07C67/287C07C69/63C07C231/12C07C233/15C07D333/12
CPCC07B39/00C07C17/00C07C17/02C07C29/62C07C67/287C07C67/307C07C231/12C07D333/12C07C22/04C07C22/08C07C33/423C07C69/76C07C69/63C07C233/15
Inventor 刘艳黄达涯黄菊丸岡啓二
Owner GUANGDONG UNIV OF TECH
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