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Synthetic method of olefin compound

A synthetic method and compound technology, applied in the direction of organic chemistry, can solve problems such as limited application, and achieve the effect of simple preparation method, simple operating conditions, and easy operation

Active Publication Date: 2017-07-11
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The resulting trisubstituted alkenes limit their application in organic synthesis
Despite these advances, through C(sp 3 The reaction of )-H bonds with terminal alkynes to obtain disubstituted alkenes is a very big challenge

Method used

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  • Synthetic method of olefin compound
  • Synthetic method of olefin compound
  • Synthetic method of olefin compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1～10

[0042]Add fatty acid amide (0.1mmol), acetylene compound (0.4mmol), nickel acetate (0.02mmol), methyldiphenylphosphine (0.04mmol), acetic acid (0.2 mmol) and sodium acetate (0.05mmol) and organic solvent 0.5ml, change nitrogen three times, mix and stir evenly, after completing the reaction according to the reaction conditions of Table 2, cooling, suction filtration, silica gel sample mixing, obtain corresponding through column chromatography purification Disubstituted olefin compound (I), the reaction process is shown in the following formula:

[0043]

[0044] The raw material proportioning of table 1 embodiment 1~12

[0045]

[0046]

[0047] The reaction condition and reaction result of table 2 embodiment 1~12

[0048]

[0049] a use PPh 3 Ligand MePh 2 P;

[0050] b Replace catalyst nickel acetate with nickel iodide;

[0051] In Table 1 and Table 2, T is the reaction temperature, t is the reaction time, 4-Fbenzyl is para-substituted benzyl, 2-naphthyl is...

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PUM

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Abstract

The invention discloses a synthetic method of an olefin compound. The method comprises the following steps: adding a fatty acid amide derivative, an acetylene derivative, nickel acetate, methyldiphenylphosphine, sodium acetate and acetic acid into an organic solvent, heating the obtained solution, carrying out a reaction, and carrying out post-treatment after the reaction is completed in order to obtain the disubstituted olefin compound. The method allows the sp<3>C-H bond activation and the alkenylation of the fatty acid amide derivative and the acetylene derivative to be simultaneously carried out by using a specific catalyst, a ligands, an acid and an alkali additive. The method has the advantages of simple operating conditions and high reaction yield. The method allows the olefin compound to be efficiently synthesized, and the 8-aminoquinoline guiding group in the obtained olefin product can be removed under very mild conditions.

Description

technical field [0001] The invention belongs to the field of organic synthesis, in particular to a nickel-catalyzed sp 3 Stereoselective synthesis of alkenes by carbon-hydrogen bond activation and reaction with terminal alkynes. Background technique [0002] Functionalized olefin derivatives are powerful building blocks in organic synthesis, for example, it can be used in different cross-coupling reactions, cycloaddition reactions, and metathesis reactions and other application examples. The raw materials of the traditional method of synthesizing olefins usually need to be pre-functionalized, such as Mizoroki-Heck, Suzuki, Negishi, and Stille reactions, and these reactions are complicated to operate and produce a lot of metal waste. From the consideration of atom economy, transition metal-catalyzed C–H bond activation is an ideal method to construct olefinic compounds. In the past few years, although many C(sp) catalyzed by different transition metals have been reported 2...

Claims

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Application Information

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IPC IPC(8): C07D215/40C07D409/12
CPCC07D215/40C07D409/12
Inventor 张玉红林聪陈铮凯刘占祥
Owner ZHEJIANG UNIV
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