Preparation method of aryl acetamide compound

Abstract

The invention discloses a preparation method of an aryl acetamide compound. The method comprises the following steps: adding a palladium catalyst, a ligand, benzyl formate, tertiary amine and trifluoroacetic anhydride into an organic solvent, performing reacting at 130 DEG C for 24 hours, and after the reaction is completed, carrying out after-treatment to obtain the aryl acetamide compound. The preparation method is easy to operate, the after-treatment is simple and convenient, reaction initial raw materials are cheap and easily available, benzyl formate is taken as both a carbon monoxide source and a reactant, tertiary amine is taken as an amine source, substrate designability is high, substrate functional group tolerance range is wide, and reaction efficiency is high. What is noteworthyis that C-N bonds of the tertiary amine are broken in the reaction, no extra oxidizing agent is needed, various aryl acetamide compounds can be synthesized according to actual needs, and practicability is high.

Description

technical field [0001] The invention belongs to the field of organic synthesis, in particular to a preparation method of aryl acetamide compound. Background technique [0002] Amide compounds are a very important class of skeleton molecules, which exist in a variety of natural products, drugs and functional molecules (Chem. Rev. 1997, 97, 2243-2266). Amide chemistry is an important part of organic chemistry. The functionalization of amide C-N bonds is ubiquitous in the synthesis of peptides, polymers, natural products, pesticides, and advanced materials, and is of great significance in organic synthesis (Chem.Soc.Rev. 2016, 45, 1257-1272). Arylacetamide, as a kind of amide, has attracted widespread attention because of its excellent physiological and pharmacological activities (Chem. Rev. 2010, 110, 1082-1146). [0003] The methods for synthesizing aryl acetamide compounds reported in the literature are mainly to directly obtain aryl acetamide compounds through the amidati...

AI Technical Summary

Problems solved by technology

However, C–N bond activation of tertiary amines is still a big challenge compared with primary and secondary amines.

So far, there are few reports on the carbonylation reaction of tertiary amine C-N bond breaking. Although this type of reaction provides an effective way for the synthesis of amides, there are still some disadvantages, such as under certain reaction conditions, containing excess oxidant, explosive CO / O 2 mixture etc.

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