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A method for highly selective synthesis of 1-iodoalkynes

A technology of iodine and hypervalent iodine, applied in the field of highly selective synthesis of 1-iodoalkyne, can solve the problems of using metal catalysts, harsh reaction conditions, uncontrollable reaction, etc., achieving single product, mild reaction conditions, easy separation and purification Effect

Active Publication Date: 2020-06-09
GUANGDONG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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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-iodoalkynes
  • A method for highly selective synthesis of 1-iodoalkynes
  • A method for highly selective synthesis of 1-iodoalkynes

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032]

[0033] Dissolve 38 μL (0.3 mmol) of p-methylphenylacetylene and 133 mg (0.36 mmol) of tetrabutylammonium iodide (TBAI) in 3 mL of acetonitrile, then add 96.6 mg (0.3 mmol) of iodobenzenediacetic acid in portions within 30 min into the reaction 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 71.9 mg of yellow liquid product 1 with a yield of 99%. The NMR data are as follows:

[0034] ( 1 H NMR, 400MHz, CDCl 3 , ppm): δ=7.32(d, J=8.0Hz, 2H), 7.10(d, J=8.0Hz, 2H), 2.34(s, 3H);

[0035] ( 13 C NMR, 100MHz, CDCl 3 , ppm): δ=139.1, 132.3, 129.0, 120.4, 94.3, 21.6.

Embodiment 2

[0037]

[0038] 33 μL (0.3 mmol) of phenylacetylene and 133 mg (0.36 mmol) of tetrabutylammonium iodide were dissolved in 3 mL of acetonitrile, and then 96.6 mg (0.3 mmol) of iodobenzenediacetic acid was added to the reaction system in batches within 30 min. After reacting at room temperature for 24 h, and then extracting three times with ethyl acetate, the organic phases were combined 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 62.6 mg of yellow liquid product 2 with a yield of 92%. The NMR data are as follows:

[0039] 1 H NMR (400MHz, CDCl 3 ,ppm): δ=7.41-7.43(m,2H),7.29-7.31(m,3H);

[0040] 13 C NMR (100 MHz, CDCl3, ppm): δ = 132.4, 128.8, 128.3, 123.4, 94.2, 6.2.

Embodiment 3

[0042]

[0043] Dissolve 34.4 μL (0.3 mmol) of 4-fluorophenylacetylene and 133 mg (0.36 mmol) of tetrabutylammonium iodide in 3 mL of acetonitrile, then add 193.3 mg (0.6 mmol) of iodobenzenediacetic acid to the reaction in batches within 30 min In the system, react at room temperature for 2 h, and 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 67.8 mg of yellow liquid product 3 with a yield of 92%. The NMR data are as follows:

[0044] 1 H NMR (400MHz, CDCl 3 , ppm): δ=7.42-7.40(m, 2H), 7.01(t, J=8.8Hz, 2H);

[0045] 13 C NMR (100MHz, CDCl 3 , ppm): δ=162.7 (d, J=249Hz), 134.3 (d, J=8.4Hz), 119.5 (d, J=3.5Hz), 115.7 (d, J=22.1Hz), 93.0, 5.9.

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Abstract

The invention belongs to the technical field of synthetic chemistry and particularly relates to a method for synthesizing 1-iodo-alkyne 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-iodoalkyne 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, Grignard reage...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07B39/00C07C22/04C07C17/14C07C22/08C07C21/22C07C33/42C07C29/62C07C69/76C07C67/307C07C67/287C07C69/145C07C233/07C07C231/12C07D333/12C07F7/08
CPCC07B39/00C07C17/14C07C29/62C07C67/287C07C67/307C07C231/12C07D333/12C07F7/081C07F7/083C07C22/04C07C22/08C07C21/22C07C33/426C07C69/76C07C69/145C07C233/07
Inventor 刘艳黄达涯王德安黄菊赖炳森丸岡啓二
Owner GUANGDONG UNIV OF TECH
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