Method for high-efficiency preparation of an o-hydroxyphenyl heterocyclic derivative through C-H/C-H oxidative coupling reaction based on transition metal catalysis

Abstract

The invention relates to a method for high-efficiency preparation of an o-hydroxyphenyl heterocyclic derivative through C-H / C-H oxidative coupling reaction based on transition metal catalysis. According to the method, the derivative is prepared from C-H of a phenol derivative and C-H of a heterocyclic derivative through direct one-step coupling without any activation step. Compared with the prior art, the method provided by the invention has the following advantages: the method is simpler, highly efficient and environment friendly and prevents production of considerable waste; atom economy is improved; tolerance of reaction function groups is good; organic synthesis steps are simple and concise; complicated process of pre-activation of a substrate is omitted; total yield of synthesis is improved; total cost and operation difficulty are reduced; and a molecular library of the o-hydroxyphenyl heterocyclic derivative can be highly-efficiently and rapidly obtained, and post-modification of phenol natural products can be realized, so novel drugs and candidate molecules of materials can be synthesized.

Description

technical field [0001] The invention relates to a method for efficiently preparing o-hydroxyphenyl heterocyclic derivatives based on transition metal-catalyzed C-H / C-H oxidative coupling reaction. Background technique [0002] O-hydroxyphenyl heterocyclic derivatives are a very important class of drugs, natural products, active biomolecules, organic optoelectronic materials and so on. The research on its synthesis method has been highly valued and concerned by academic circles and industries all over the world [see: (a) Hsieh, C.-C., Jiang, C.-M., Chou, P.-T. Acc. Chem. Res. 2010, 43 , 1364; (b) Kwon, J. E., Park, S. Y. Adv. Mater. 2011, 23 , 3615; (c) Demchenko, A. P., Tang, K.-C., Chou, P.-T. Chem. Soc. Rev. 2013, 42 , 1379.]. At present, there are three main methods for synthesizing o-hydroxyphenyl heterocyclic derivatives: the traditional condensation reaction, through the condensation reaction of amino groups, aldehyde groups, carboxyl groups, etc. under hars...

AI Technical Summary

Problems solved by technology

The direct C-H / C-H cross-oxidative coupling reaction can be used to post-modify phenolic natural products (estrolone, amino acids, etc.), phenolic fluorescent molecules (7-hydroxycoumarin, fluorescent green, Sudan red, etc.), thereby Improve its drug activity and fluorescence properties, while traditional synthesis methods are difficult or even impossible to complete such target molecules, highlighting the charm of C-H / C-H cross-oxidative coupling reactions in synthetic chemistry [see: Wencel-Delord, J., Glorius , F. Nature Chem. 2013,5, 369. ]

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