Method for preparing carboxylate compounds

Abstract

The invention discloses a method for preparing carboxylate compounds. According to the method, an ionic iron (III) complex which has a molecular formula of [(tBuNCH2CH2NtBu)CH][FeBr4] and contains 1,3-di-tert-butyl-imidazoline cations is taken as a catalyst, di-tert-butyl peroxide is taken as an oxidizing agent, and corresponding benzyl ester carboxylate or allylic ester carboxylate is synthesized by respectively carrying out oxidative cross-coupling on carboxylic acid and alkylbenzene, methyl heterocyclic aromatic hydrocarbon and allyl hydrocarbon compounds; applicable carboxylic acid substrates relate to aliphatic carboxylic acid, aromatic carboxylic acid and heterocyclic carboxylic acid, and applicable hydrocarbon compounds relate to benzyl type compounds and allyl type compounds. The method is the first case for preparing carboxylate by virtue of the oxidative cross-coupling of carboxylic acid, alkylbenzene, methyl heterocyclic aromatic hydrocarbon and allyl hydrocarbon compounds through iron-based catalysts; compared with literature reports, the method has the advantages that the catalytic efficiency is relatively high, and the substrate applicability is relatively wide.

Description

technical field [0001] The invention belongs to the technical field of preparation of organic compounds, and in particular relates to a catalytic preparation method of carboxylic acid ester compounds. Background technique [0002] Carboxylate compounds are important building blocks of many natural products, pharmaceutical molecules and fine chemicals (see: K.C.K. Swamy, N.N.B. Kumar, E. Balaraman, K.V.P.P. Kumar, Chem. Rev., 2009,109,2551), so the synthesis of carboxylic acid esters has received more and more attention. These compounds are traditionally prepared by reacting carboxylic acids or carboxylic acid derivatives (such as acid chlorides or anhydrides) with alcohols, or by reacting carboxylate salts with halogenated hydrocarbons, but these methods often have significant drawbacks , For example, the reversibility of the reaction, the harsh reaction conditions, the discharge of halogen-containing waste, the limitation of the substrate, etc., all of which need to be fur...

AI Technical Summary

Problems solved by technology

Using di-tert-butyl peroxide as the oxidant and iron acetylacetonate as the catalyst, the first iron-based catalyst catalyzed the esterification reaction of carboxylic acid and cyclic ether compound, but unfortunately, the catalyst is not suitable for the esterification reaction involving toluene No catalytic activity, poor activity on allyl hydrocarbons

In short, there is no esterification reaction of carboxylic acid, toluene compound and heterocyclic aromatic hydrocarbon realized by iron-based catalyst.

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