Axial-chirality bidentate ligand and application thereof in copper-catalyzed coupling reaction

Abstract

The invention discloses an axial-chirality bidentate ligand and application thereof in a copper-catalyzed coupling reaction. The structural formula of the axial-chirality bidentate ligand is shown inthe original specification, wherein R is 2-Me or 3-Ome or 32-t-Bu or 32-F or 32, 3, 4-F. The application of the axial-chirality bidentate ligand in the copper-catalyzed coupling reaction comprises thefollowing steps: stirring the ligand and copper salt in diethyl ether for coordination, concentrating and performing spin drying, so as to obtain a catalyst; adding trimethoxyphenyl-silicon and bromobenzene into a 10mL single aperture reaction flask, adding ethanol into the reaction flask for dissolving, adding alkali into the reaction flask and 5mol% of the catalyst, rising the temperature of the reaction to 60-100 DEG C, performing a reaction for 6-12h and directly performing column chromatography after the reaction is ended, so as to obtain a white solid product. According to the axial-chirality bidentate ligand and the application thereof in the copper-catalyzed coupling reaction, the technical problem that how the relatively high yield is obtained under a mild condition can be solved.

Description

technical field [0001] The invention belongs to the field of metal catalysis, and in particular relates to an axial chiral bidentate ligand and its application in Nozaki-Hiyama-Kishi decarboxylation C-C coupling reaction. Background technique [0002] In recent years, the metal palladium-catalyzed decarboxylation coupling reaction has received more and more attention, and great research progress has been made, especially in the synthesis of diaryl compounds. For example, Germany The BASF company of the BASF company has discovered a new drug with a good inhibitory effect on fungi by using the synthesis technology of diaryl compounds. [0003] Goossen et al. reported that palladium catalyzed the decarboxylation of 2-nitrobenzoic acid and the coupling of bromobenzene to prepare diaryl compounds. This study provided a method for the preparation of biphenyl compounds by decarboxylation. The key synthesis steps of new drug pharmaceutical intermediates, the reaction steps are as f...

AI Technical Summary

Problems solved by technology

[0007] After a long period of scientific research and exploration, researchers have gradually solved the limitation that organotin reagents, organozinc reagents, grittin reagents and other organometallic reagents were used in the synthesis of biaryl compounds, reducing the environmental hazards of heavy metals, but There are still some limitations. Generally, the catalyst needs noble metal catalysts such as palladium, and the synthesis cost is relatively high, which restricts the large-scale application of this reaction.

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