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Method for synthesizing olefin through selective desaturation of inert carbon-carbon bonds

A carbon-carbon bond, selective technology, applied in chemical instruments and methods, preparation of organic compounds, organic chemistry, etc., can solve the problems of harsh reaction conditions, low selectivity and efficiency, and limited substrate range, and achieve reaction efficiency. High, high application value, good effect of regional selectivity

Active Publication Date: 2021-07-27
YANGZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the method suffers from low selectivity and efficiency, limited substrate range, and harsh reaction conditions

Method used

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  • Method for synthesizing olefin through selective desaturation of inert carbon-carbon bonds
  • Method for synthesizing olefin through selective desaturation of inert carbon-carbon bonds
  • Method for synthesizing olefin through selective desaturation of inert carbon-carbon bonds

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] Embodiment 1: Add 0.2mmol chloroamide 1a, [RuCl 2 (p-cymene)] 2 (10mol%, 12.8mg), ligand L1 (20mol%), KOAc (0.4mmol, 40mg), H 2 O (1mmol, 18mg), was added with 1,2-dichloroethane (4mL) for lyophilization and deoxygenation, under nitrogen protection. Seal the tube, and react under the irradiation of 38W 460nm blue light for 48 hours unless otherwise specified. After the reaction, the reaction mixture was concentrated to obtain a crude product, which was purified by column chromatography to obtain olefinic compound 2a. The yield is 58% yield, E / Z≧20 / 1, and the E / Z ratio is obtained from the integral ratio of the isomer olefin hydrogen atom characteristic signal peaks in the H NMR spectrum of the crude product.

[0033] 1 H NMR (400MHz, CDCl 3 )δ7.38(d, J=7.4Hz, 2H), 7.32(t, J=7.4Hz, 2H), 7.23(d, J=7.2Hz, 1H), 6.50(d, J=15.9Hz, 1H) ,6.29(dt,J=15.8,7.3Hz,1H), 5.42(s,1H),3.07(d,J=8.4Hz,2H),1.35(s,9H).

[0034] 13 C NMR (101MHz, CDCl 3 )δ169.9, 136.7, 134.1, 128.6, 1...

Embodiment 2

[0037] Example 2: On the basis of Example 1, replace L1 (20 mol%) with L2 (20 mol%), and the rest are the same as Example 1 to synthesize compound 2a with a yield of 26%, E / Z≧20 / 1.

Embodiment 3

[0038] Example 3: On the basis of Example 1, replace L1 (20 mol%) with L3 (20 mol%), and the rest are the same as Example 1 to synthesize compound 2a with a yield of 49%, E / Z≧20 / 1.

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Abstract

The invention relates to a method for synthesizing olefin by selective desaturation of inert carbon-carbon bonds. The method comprises the following steps of: synthesizing a chlorinated amide compound serving as a raw material in the presence of visible light, a ruthenium catalyst and a ligand, and post-treating reaction liquid to obtain a remote alkenyl amide compound. In the presence of the ruthenium catalyst and the phenylpyridine ligand, intramolecular carbon-hydrogen bond activation of the amide compound is successfully realized, and the remote olefin compound is synthesized; according to the method, chloro-amide which is simple and easy to obtain is used as a raw material, the substrate application range is wide, and the reaction efficiency is high; in the free radical migration process, 1, 5 migration occurs all the time along with beta-H elimination, terminal alkene and conjugated double bonds are used as main products, and high regioselectivity is achieved; and the maximum E / Z value of the obtained olefin compound is greater than 20: 1, and the stereoselectivity is good. The double bond of the compound can be further converted into other functional groups, the conversion process is simple in one step, and the obtained derivative can be used as a medical intermediate and has high potential application value.

Description

technical field [0001] The invention relates to the technical field of organic compound synthesis, in particular to a method for synthesizing olefins through selective desaturation of inert carbon-carbon bonds. Background technique [0002] Alkenes are one of the most widely used functional groups in organic synthesis. They are widely found in various bioactive molecules and natural products. As powerful precursors for the construction of other functional group compounds, olefins are versatile synthetic materials and their derivatives. As a precursor, alkenes have many applications in biochemistry and other fields, and at the same time, they are also a stable, effective and cheap raw material. Different alkenes have specific skeletons, and the chemical units (C=C double bond, aryl group at the C-1 position of the double bond or other substituents) provide favorable conditions for participating in the construction of heterocyclic compounds of different sizes. Furthermore, it...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C231/12C07D209/48C07D211/58C07D309/14C07D333/24C07C233/11C07C233/13C07C233/51C07C235/34C07C233/65C07B35/04
CPCC07C231/12C07D209/48C07D211/58C07D309/14C07D333/24C07B35/04C07C2602/28C07C2601/02C07C2601/14C07C2603/74C07C233/11C07C233/13C07C233/51C07C235/34C07C233/65
Inventor 王传勇邢仲秋
Owner YANGZHOU UNIV
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