Method for synthesizing boron (silicon) alkylated indole and tetrahydroquinoline through one-pot method

Abstract

The invention discloses a method for synthesizing boron (silicon) alkylated indole and tetrahydroquinoline through a one-pot method, and belongs to the technical field of organic synthesis. Accordingto the method, indole, quinoline and catechol borane are used as raw materials, and are subjected to a reaction for 0.5-48 h at a room temperature by using tris(pentafluorophenyl) boron (B(C6F5)3) asa catalyst to simultaneously obtain 3-position boron alkylated indole and tetrahydroquinoline; or indole, quinoline, catechol borane and silane are used as raw materials, and are subjected to a reaction for 0.5-48 h at a room temperature by using tris(pentafluorophenyl) boron (B(C6F5)3) as a catalyst to simultaneously obtain 3-position silicon alkylated indole and tetrahydroquinoline. According tothe present invention, 3-position boron (silicon) alkylated indole and tetrahydroquinoline are simultaneously obtained through the one-pot method, such that the method has characteristics of high functional group tolerance, wide substrate applicability, easily available raw materials, convenient operation, mild reaction conditions, rapidness, high yield and the like.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a one-pot catalytic system, which can simultaneously synthesize boron (silicon) alkylated indole and tetrahydroquinoline. Background technique [0002] Selective functionalization of carbon-hydrogen bonds is an important means to realize the diversity of organic molecules, and has always been a hot and difficult research topic in the field of organic synthesis. Indole organoboron (silicon) compounds often have flexible and changeable properties, and are widely used in the fields of synthetic chemistry, materials chemistry, and biomedical chemistry (D.G.Hall et al., Wiley–VCH, Weinheim, 2011; D.R. Spring et al., Chem. Soc. Rev. 2012, 41, 1845-1866.). Tetrahydroquinoline and its derivatives are a class of important biologically active compounds, and are important structural units and intermediates in the synthesis of alkaloids, drugs and agricultural chemical...

AI Technical Summary

Problems solved by technology

The current technical status is that the reaction conditions are harsh (such as the reaction requires heating, the amount of catalyst used is large, the use of precious metals is used for catalysis, etc.), the atomic efficiency is low (a large number of by-products are generated), there are many side reactions that are difficult to suppress, and the product yield is not high ( J.F. Hartwig et al., Chem. Rev. 2015, 115, 8946-8975)

And the synthetic of tetrahydroquinoline compound, mainly take hydrogen as hydrogen source, metal or metalloid catalyst catalyzes, usually needs harsh reaction conditions such as high temperature, high pressure, excessive use reducing agent, causes bigger waste (Zhou Yonggui etc., Chem. Rev., 2012, 112, 2557–2590.; D.W. Stephan et al., Chem. Soc. Rev., 2019, 48, 3592-3612)

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