Method for electrochemical synthesis of isocoumarin compound

Abstract

The invention discloses a method for synthesizing an isocoumarin compound through electrochemical oxidative dehydrogenation coupling, and belongs to the technical field of organic chemistry. In a non-separated electrolytic tank, substituted aryl formic acid 1 and an alkyne compound 2 are subjected to a constant-current electrolytic reaction in an organic solvent in the presence of an iridium catalyst and an additive to obtain an isocoumarin derivative 3. According to the method disclosed by the invention, a C-O / O-H bond cyclization product is obtained with high selectivity under the condition of electric anodic oxidation and the catalysis of transition metal iridium. The method is mild in reaction condition, environment-friendly, high in yield and good in purity, and a simple and effective synthesis way is provided for the isocoumarin compound.

Description

technical field [0001] The invention relates to a preparation method of isocoumarin-containing derivatives, in particular to a method for synthesizing isocoumarin compounds through electrochemical oxidative dehydrogenation coupling, and belongs to the field of organic chemistry. Background technique [0002] Isocoumarins are an important class of natural lactones that exist in a variety of natural products and have various biological activities, such as antifungal, antitumor, antiallergic, antimicrobial, anti-inflammatory and anticancer activities. Isocoumarins are also essential intermediates in the synthesis of many other compounds such as isoquinolines, isocarbitin and isochromones. [0003] Traditional methods for the synthesis of such compounds employ transition metal-catalyzed cyclization of ortho-halogenated aromatic esters or carboxylic acids with π-electron components. Among the methods reported in the existing literature, transition metal (Rh, Ir, Ru) catalyzed di...

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Problems solved by technology

[0006] In order to overcome the existing problems in the prior art: 1) weakly coordinated aryl carboxylic acid C-H bond selectivity is poor, 2) defects such as the use of a large amount of oxidant, the invention discloses a novel isocoumarin compound Preparation method; the preparation method can obtain the cyclization product by C-O / O-H bond with high selectivity under the condition of electric anodic oxidation and under the catalysis of transition metal iridium; the method has mild reaction conditions, environment-friendly, high yield, good purity, suitable for industrial production

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