Method using aryl diazonium tetrafluoroborate and nitrile to prepare organic amide compounds

Abstract

The method provides a method for efficiently synthesize organic amide compounds containing different substitution functional groups in a high selectivity manner. The method is characterized in that copper iodide is used as the catalyst, aryl diazonium tetrafluoroborate compounds and organic nitrile compounds are used as the reaction substrates, and an organic solvent, water and alkali are added into the reaction system. The method has the advantages that the catalyst is cheap and easy to obtain; the substrates are high in adaptability; reaction conditions are mild, safe and reliable; the selectivity of the obtained target product is close to 100%, and the yield of the target product reaches up to 90% or above; defects that a traditional method for synthesizing the organic amide compounds is harsh in reaction condition, poor in reaction selectivity, complex in experiment steps and low in yield, needs reagents harmful to environments and the like are overcome, and the method is promisingin industrial application prospect. The invention further provides the corresponding organic amide compounds containing different substitution functional groups.

Description

【Technical field】 [0001] The invention relates to the field of catalytic synthesis of organic amide compounds, in particular to a method for efficiently preparing organic amide compounds and their derivatives by using aryl diazonium tetrafluoroborate and organic nitrile compounds. 【Background technique】 [0002] Organic amides are important intermediates in organic synthesis. They are widely used in the preparation of pharmaceutical structural substances, polymer intermediates, photoelectric materials, flame retardants, and pesticides. The amide bond is one of the most basic chemical structures found in nature, which constitutes the backbone of important biological peptides and proteins, and exists in many natural products and compounds such as drugs. In 2011, sampling statistics were made on the compounds developed by the three major international pharmaceutical companies, and nearly 54% of the compounds had amide bonds. [0003] Using carboxylic acid and organic amine to...

AI Technical Summary

Problems solved by technology

In addition to the above-mentioned traditional methods, the synthesis methods of organic amides reported in the literature mainly include: (1) using halogenated hydrocarbons, amines and carbon monoxide to efficiently achieve carbonyl insertion reactions to prepare corresponding amides; (2) using benzyl (3) transition metal-catalyzed efficient coupling-hydration reaction of alkynes with primary amines and water; (4) transition metal-catalyzed organic carboxylic acids and tertiary amines through C-N bond breaking and efficient coupling to prepare organic amides; (5) three-component cross-coupling reaction of organometallic reagents (organozinc, organomagnesium, etc.) with acid chlorides and ammonia; (6) transition metal catalyzed halogenated aromatics Coupling-hydration reaction with nitrile compounds; however, the above methods generally use noble metal reagents and air-sensitive reagents, and there are also cumbersome experimental steps, expensive catalysts and difficult recycling, harsh reaction conditions, and cross-substrate applicability. , lower yield and greater environmental pollution