Method for functionalization modification of benzyl hydrogen of benzyl-containing compound with C-C double bonds or carbonyl groups

Abstract

The invention discloses a method for functionalization modification of benzyl hydrogen of a benzyl-containing compound with C-C double bonds or carbonyl groups. According to the method, the benzyl-containing compound and dimethyl sulfoxide are subjected to a one-pot reaction in the presence of ammonium persulfate and sodium methylate in a protective atmosphere so as to obtain a styrene derivative;or the benzyl-containing compound and dimethyl sulfoxide are subjected to a one-pot reaction in the presence of potassium persulfate and sodium methylate in an air environment so as to obtain a phenyl ketone derivative. The method realizes high-yield high-selectivity modification of benzyl hydrogen of the benzyl-containing compound with C-C double bonds or carbonyl groups under nonmetal catalyticand mild reaction conditions through one-step reaction; and the method is simple in step, short in process flow, low in cost and beneficial for industrial production.

Description

technical field [0001] The invention relates to a method for benzyl hydrogen functionalization of benzyl compounds, in particular to a method for modifying carbon-carbon double bonds or carbonyl groups with benzyl hydrogen functionalization of benzyl compounds, belonging to the field of organic synthesis. Background technique [0002] Functional modification is a commonly used method in organic synthesis, especially in drug synthesis. Due to the existence of the conjugated benzene ring, the benzyl hydrogen is relatively active and easy to modify, which provides a new idea for drug synthesis and has become a research hotspot for many years. Most of the previous research is to substitute on the benzyl hydrogen to modify the functional group. At present, there are reports (such as: literature "Angew.Chem.Int.Ed.2012,51,2745-2748", "Angew.Chem.Int.Ed.2015,54,1261-1265", "Green Chem., 2015 , 17, 2369-2372", "Org.Lett.2015, 17, 2078-2081"), discloses that 2-benzylpyridine is use...

AI Technical Summary

Problems solved by technology

[0004] In addition, there are literature reports (for example, literature "Org.Lett.2014, 16, 2050-2053", "Chem.Commun.2014, 50, 7636-7638"), with 2-benzylpyridine as raw material, with DMF or DMAc is a methyleneization reagent, potassium persulfate or sodium persulfate is an oxidizing agent, reacts under the catalysis of a copper catalyst, and modifies the carbon-carbon double bond on 2-benzylpyridine benzyl hydrogen, although these methods can obtain higher Selectivity, but it requires the use of transition metal catalysts, which has a large impact on the environment and high cost, (such as reactions 5 and 6)

Images