Preparation method of phosphine ligand and method for phosphine ligand to catalyze and synthetize biaryl and derivatives thereof

Abstract

The invention relates to a preparation method of phosphine ligand and a method for the phosphine ligand to catalyze and synthetize biaryl and derivatives thereof. The preparation method of the phosphine ligand comprises the following steps: 2-diphenyl phosphono benzaldehyde is used to react with a Grignard reagent, and the phosphine ligand is acquired; X in the Grignard reagent is halogen, and R is C1-C8 alkyl, aryl or substituted aryl; wherein, the substituted aryl is that one or multiple positions in number 2 to 6 positions of aromatic ring are substituted; and substituent is one or varieties in fluorine, chlorine, phenyl, C1-C8 alkyl and C1-C8 alkoxy. The invention discloses the method of using the phosphine ligand to jointly catalyze and synthetize the biaryl and the derivatives thereof with a nickel catalyst. The invention uses high catalytic activity of the phosphine ligand, TON is usually higher than 2500, and the phosphine ligand is easy to be prepared and suitable for industrial production. The phosphine ligand can be produced by the Grignard reagent and 2-diphenyl phosphono-containing benzaldehyde in the field without separation, and directly catalyze a coupling reaction; and furthermore, the reactivity of the phosphine ligand is not obviously reduced.

Description

technical field [0001] The present invention relates to a method for preparing a phosphine ligand and a method for catalytically synthesizing biaryls and derivatives thereof, in particular to a method for preparing a class of phosphine ligands, and using the phosphine ligands and a nickel catalyst to jointly catalyze the synthesis of biaryls and biaryls. method of its derivatives. Background technique [0002] Biaryl compounds are a class of functional and versatile compounds, often used in liquid crystal materials and pharmaceutical intermediates. For example: 3, 4, 3", 4"-tetramethyl terphenyl is used in conductive polymer materials, and 4'-methyl biphenyl-2-carbonitrile is an intermediate of sartan drugs. [0003] Commonly used synthetic methods for biaryls include the reaction of aryl diazonium salts with aromatics under the catalysis of copper (I) to generate biaryls. When there are electron-withdrawing groups on each benzene ring, it is difficult to synthesize the de...

AI Technical Summary

Problems solved by technology

[0003] Commonly used synthetic methods for biaryls include the reaction of aryl diazonium salts with aromatics under the catalysis of copper (I) to generate biaryls. When there are electron-withdrawing groups on each benzene ring, it is difficult to synthesize the desired product by this method.

[0004] Another method is to use Suzuki coupling reaction, that is, aryl boronic acid or its ester is coupled with halogenated aromatic hydrocarbon under the catalysis of transition metal to generate biaryl hydrocarbon. This method has very wide adaptability and can tolerate many functional groups. The catalyst uses various This reaction can be catalyzed by Pd(O), Ni(O) complexed by a kind of ligand, even metal complexes such as Mn and Fe, but the preparation of phenylboronic acid or its ester, one of the main raw materials of its reaction, is relatively difficult. The price is high, the catalysts used are all homogeneous Pd catalysts, and the recovery of catalysts is difficult

Images