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Method for preparing diaromatic hydrocarbon from aromatic hydrazine

A technology for aromatic hydrazine and biaromatic hydrocarbons, which is applied in the field of aromatic hydrazine to prepare biaromatic hydrocarbons, can solve the problems of high reaction temperature of phenylhydrazine self-coupling side reaction, inability to exclude silane self-coupling side reaction, and the universality of the reaction has not been investigated. , to achieve high practicability and selectivity, inhibition of self-coupling reaction, mild reaction conditions

Inactive Publication Date: 2015-12-23
SHAOXING UNIVERSITY
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  • Abstract
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Problems solved by technology

However, there are many problems in this isolated example: (1) the reaction efficiency is not high (2) the universality of the reaction has not been investigated (3) the reaction cannot exclude the occurrence of side reactions of silane self-coupling and phenylhydrazine self-coupling ( 4) High reaction temperature

Method used

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  • Method for preparing diaromatic hydrocarbon from aromatic hydrazine
  • Method for preparing diaromatic hydrocarbon from aromatic hydrazine
  • Method for preparing diaromatic hydrocarbon from aromatic hydrazine

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Embodiment 1～12

[0037] Add 1mmol of aromatic hydrazine, 1.2mmol of aryl silicon ether, 0.05mmol of divalent palladium catalyst and 1mmol of camphorsulfonic acid (CSA) into a round-bottomed flask containing 1ml of TBAF (1M) in tetrahydrofuran, and stir at 50°C for 3 hours . Cool down to room temperature after completion of the reaction, filter out the solid, spin dry the solvent, and separate the column to obtain the product. The raw materials, catalysts and reaction results used are shown in Table 1.

[0038] The used raw material and catalyst kind of table 1 embodiment 1~14

[0039]

[0040]

[0041] Some product characterization data are as follows:

[0042] 1-Phenylnaphthalene:

[0043]

[0044] Whitesolid, m.p.41-42℃ (lit. 2 mp41-43°C); 1 HNMR (400MHz, CDCl 3 , TMS) δ7.91(t, J=8.0Hz, 1H), 7.59(d, J=8.0Hz, 2H), 7.48-7.54(m, 3H), 7.40-7.47(m, 5H), 7.32(t ,J=7.2Hz,1H). 13 CNMR (100MHz, CDCl 3 , TMS) δ141.06, 140.57, 134.10, 131.92, 130.31, 128.57, 127.94, 127.56, 127.23, 126....

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Abstract

The present invention discloses a method for preparing diaromatic hydrocarbon from aromatic hydrazine. The method comprises that: under effects of a bivalent palladium catalyst and camphor sulfonic acid, aryl siloxane and aromatic hydrazine are subjected to a coupling reaction, and after completing the reaction, post-treatment is performed to obtain the diaromatic hydrocarbon. According to the preparation method of the present invention, the specific additive camphor sulfonic acid is added to the reaction system, such that the coupling reaction of the aryl siloxane and the aromatic hydrazine is effectively promoted, the reaction conditions are mild, the self-coupling reaction of the aryl siloxane is inhibited, and the reaction yield is improved.

Description

technical field [0001] The invention belongs to the field of chemical synthesis, and in particular relates to a method for preparing biaryl hydrocarbons from aromatic hydrazines. Background technique [0002] Biaryl compounds are a commonly used structural unit in organic synthesis. They are commonly used in the preparation of various organic compounds. At present, the methods used in the synthesis of such compounds reported in the literature are mainly transition metal-catalyzed coupling reactions, including Suzuki coupling, Negishi coupling, Stille coupling, Hiyama coupling, Kumada coupling, Ullmann coupling method, etc. (Suzuki and Negishi also won the 2011 Nobel Prize in Chemistry), so it is very necessary to study milder conditions and economically valuable. [0003] In recent years, the application of organosilicon reagents in organic synthesis has developed rapidly, attracting more and more attention from organic and medicinal chemists. Studies have shown that certa...

Claims

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Application Information

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IPC IPC(8): C07B37/00C07C1/32C07C15/24C07C15/14C07C17/263C07C25/18C07C41/30C07C43/205C07D213/16C07D213/127C07D257/04C07D333/08
Inventor 朱余玲赵保丽
Owner SHAOXING UNIVERSITY
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