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Method for preparing diaryl ketone from aryl sulfonate

A technology of aryl sulfonate and diaryl ketone, applied in the preparation of carboxylic acid nitrile, carbon monoxide reaction preparation, chemical instruments and methods, etc., can solve the complicated steps of aryl halide, the low stability of diazo compounds, Unfavorable to large-scale production and other problems, to achieve the effects of no by-products, good functional group tolerance, and wide reaction substrates

Inactive Publication Date: 2016-11-23
SHAOXING UNIVERSITY
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  • Abstract
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AI Technical Summary

Problems solved by technology

Finally, the preparation of some aryl halides requires tedious steps and harsh reaction conditions
Another part of the research focuses on aryl diazonium salts (eq 2) and aryl azide amines (eq 3). However, the low stability of diazo compounds greatly limits the wide application of this type of method (T.Saeki, E .-C. Son and K. Tamao, Org. Lett. 2004, 6, 617.)
Diaryliodonium ions are expensive and unfavorable for large-scale production as electrophiles
On the other hand, due to the stability of aryl sulfonate itself and the relative inactivity in the reaction, it is more challenging and difficult to use transition metals for oxidative addition to its carbon-oxygen bond. The transformation of compounds has great innovative significance and is also a great challenge to organic chemists

Method used

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  • Method for preparing diaryl ketone from aryl sulfonate
  • Method for preparing diaryl ketone from aryl sulfonate
  • Method for preparing diaryl ketone from aryl sulfonate

Examples

Experimental program
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Embodiment 1～12

[0037] In Examples 1-12, DMSO was used as the reaction solvent, benzenesulfonate and phenylboronic acid were used as substrates, and different catalysts were used for the reaction. The reaction conditions and results are shown in Table 1.

[0038] The reaction condition and reaction result of table 1 embodiment 1~12

[0039]

Embodiment 13～20

[0041] Examples 13-20 use triphenylphosphine palladium acetate as a catalyst, benzenesulfonate and phenylboronic acid as substrates, and react by using different solvents. See 2 for the reaction conditions and reaction results.

[0042] The reaction conditions and reaction result of table 2 embodiment 13~20

[0043]

Embodiment 21～26

[0045] In Examples 21 to 26, triphenylphosphine palladium acetate was used as a catalyst, DMSO was used as a reaction solvent, and different tosylates were used as substrates for the reaction. See 3 for the reaction conditions and results.

[0046] The reaction condition and reaction result of table 3 embodiment 21~26

[0047]

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Abstract

The invention discloses a method for preparing diaryl ketone from aryl sulfonate. The method includes following steps: in the presence of a catalyst and carbon monoxide, allowing aryl sulfonate and aryl boronic acid to react in an organic solvent; after reaction is finished, performing aftertreatment to obtain diaryl ketone. Aryl sufonate is adopted as an electrophilic reagent for Suzuki cross carbonylation coupling reaction, diaryl ketone is directly synthesized through carbon monoxide, aryl sulfonate and aryl boronic acid, reaction conditions are milk, functional groups are high in tolerance, a substrate is cheap and easy to get, and diaryl ketone can be prepared with high yield.

Description

technical field [0001] The invention belongs to the field of chemical synthesis, and in particular relates to a method for preparing diaryl ketone from aryl sulfonate. Background technique [0002] Diaryl ketone compounds are a class of important additives and chemical intermediates, and have been widely used in many industries, such as medicine, pesticides, plastics, dyes, plastics, coatings, daily chemicals and electronic chemicals (Liu Zhongze, " Synthesis and application of benzophenone series products", "Fine Chemical Intermediates", 2002, 32(2): 7~8.). In terms of plastics, diaryl ketone compounds are indispensable additive components of plastic products as light stabilizers; Intermediates of modafinil and the new powerful cerebrovasodilator flunarizine; in terms of spices, because it has the scent of roses, it is often used as a spice fixative, and it is also used as a fragrance for many perfumes and soaps raw materials. [0003] The traditional synthesis of diaryl...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C45/49C07B41/06C07C49/84C07C49/813C07C49/784C07C49/786C07C49/78C07C49/80C07C253/30C07C255/56C07C201/12C07C205/45C07D213/50C07D333/22C07D241/12
CPCC07B41/06C07C45/49C07C201/12C07C253/30C07D213/50C07D241/12C07D333/22C07C49/84C07C49/813C07C49/786C07C49/78C07C49/80C07C255/56C07C205/45
Inventor 朱余玲赵保丽
Owner SHAOXING UNIVERSITY
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