Process for preparing biaryls from aromatic hydrazines

A technology for the preparation of aromatic hydrazines and biaryls, applied in the field of aromatic hydrazines to prepare bisaryls, which can solve the problems of high reaction temperature of phenylhydrazine self-coupling side reactions, silane self-coupling side reactions cannot be ruled out, and the universality of the reaction has not been investigated. , to achieve high practicability and selectivity, inhibit self-coupling reaction, and mild reaction conditions

Inactive Publication Date: 2018-09-07
SHAOXING UNIVERSITY
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

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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  • Process for preparing biaryls from aromatic hydrazines
  • Process for preparing biaryls from aromatic hydrazines
  • Process for preparing biaryls from aromatic hydrazines

Examples

Experimental program
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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 THF, and stir at 50°C for 3 Hour. Cool down to room temperature after completion of the reaction, filter out the solid, spin dry the solvent, and separate by 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] White solid, m.p.41-42℃(lit. 2 mp 41-43°C); 1 H NMR (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 C NMR (100MHz, CDCl 3 , TMS) δ141.06, 140.57, 134.10, 131.92, 130.31, 128.57, 127.94, 127.56, 127.23, 126.36, 126.01, ...

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Abstract

The invention discloses a method for preparing biaryl hydrocarbons from aromatic hydrazine, which comprises the following steps: under the action of divalent palladium catalyst and camphorsulfonic acid, aryl silicon ether and aromatic hydrazine undergo a coupling reaction, after the reaction is complete, after Processing yields the biaryls. The preparation method effectively promotes the coupling reaction of aryl silicon ether and aromatic hydrazine by adding a specific additive camphorsulfonic acid in the reaction system, the reaction conditions are milder, the self-coupling reaction of aromatic silicon ether is suppressed, and the The yield of the reaction.

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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Patent Type & Authority Patents(China)
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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