Activation method of perfluoroalkyl carbonhalogen bond and method for synthesizing pyridine derivative

Abstract

The invention discloses an activation method of a perfluoroalkyl carbon-halogen bond and a method for synthesizing a pyridine derivative. The activation method is characterized by comprising the stepthat: active pyridine-boron free radicals generated by reaction between 4-cyanopyridine and pinacol biborate are used for catalyzing the homolysis of a carbon-halogen bond of perfluoroalkyl halide toform perfluoroalkyl free radicals. Perfluoroalkyl of olefin and a pyridine difunctionalized pyridine derivatization product are obtained by reaction by taking the pinacol biborate, the perfluoroalkylhalide (or bromide), the 4-cyanopyridine and the olefin as initiators. The method for synthesizing the pyridine derivative, provided by the invention, can simultaneously introduce two important groups, namely the perfluoroalkyl and the pyridine into the olefin for the synthesis of the pyridine derivative, thereby having the value of developing a novel method for the industrial synthesis of a pyridine compound.

Description

technical field [0001] The present application relates to the technical field of organic synthesis, in particular, to a method for activating a perfluoroalkyl carbon-halogen bond and a method for synthesizing pyridine derivatives. Background technique [0002] Fluorine-containing groups can change the physical and chemical properties of substances, and are widely used in medicine, agricultural chemistry and material science, especially in medicine, and can be used as important pharmacophore. Perfluoroalkyl halides are an inexpensive and readily available source of fluorine. However, the activation of perfluoroalkyl carbon-halogen bonds is a key step to achieve the introduction of perfluoroalkyl groups into target compounds. Transition metal catalysis or photocatalysis can effectively activate perfluoroalkyl carbon-halogen bonds, generate perfluoroalkyl carbon radicals, and further realize subsequent transformations. However, these methods usually use transition metals, whi...

AI Technical Summary

Problems solved by technology

The traditional methods for introducing pyridine rings include photocatalysis or coupling reaction catalyzed by transition metals. Among them, the photocatalysis method has the advantages of mild conditions and green reaction, but the construction of the reaction device is cumbersome and it is difficult for large-scale industrial production; transition The metal method has the advantages of easy control of the reaction and simple experimental operation, but the catalyst is expensive, heavy metals remain in the product, and a large amount of waste liquid will be generated. The production cost is too high, and it does not meet the requirements of developing modern green chemical industry. Wide range of applications

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