A kind of synthetic method of organophosphorus compound

Abstract

The invention discloses a synthesis method of 5, 5', 6, 6', 7, 7', 8, 8'-octahydro[1, 1'-binaphthyl]-2, 2'-bis[diphenylphosphine] and belongs to the field of organic synthesis. The method comprises that binaphthol as a starting raw material undergoes a catalytic hydrogenation reaction, the reaction product undergoes an esterification reaction, and the esterification reaction product and diphenylphosphine undergo a C-P bond coupling reaction under co-catalysis of a palladium catalyst and a phosphine ligand to produce a target product. The synthesis method has a product yield of 35%. Compared with the prior art, the synthesis method has few steps, is free of highly toxic raw materials, is easy to separate and purify and is suitable for industrial production. The prepared target product belonging to the field of chiral catalysis and asymmetric cycloaddition has unique catalytic activity and has a wide application prospect in the field of medicine and natural product synthesis.

Description

technical field [0001] The invention relates to the technical field of organic synthesis, and relates to a method for synthesizing organic phosphorus compounds, in particular to 5,5',6,6',7,7',8,8'-octahydro-[1,1'-linked Preparation method of naphthalene]-2,2'-bis[diphenylphosphine] (hereinafter referred to as H8-BINAP). Background technique [0002] Binaphthylbisdiphenylphosphine compounds are an important class of catalyst ligands, which have a wide range of uses in the synthesis of natural products, drugs, functional materials and biologically active compounds. Catalytic C-C bond coupling [J.Am.Chem.Soc.1998,120(22),5579~5580], chiral hydrogenation [J.Am.Chem.Soc.1995,117(9),2675~2676] , cycloaddition [Angew.Chem.Int.Ed.1997,36(5),518~521] and other reactions have their unique catalytic activity. Compared with binaphthylbisdiphenylphosphine, H8-BINAP has a larger chelation angle, and the chirality induction effect is more prominent, such as Pd(CF 3 COO) 2 The catalyti...

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Problems solved by technology

The current chiral H8-BINAP method is reported by EP839819, using binaphthol as the starting material, through hydrogenation, esterification to obtain the standby product two and diphenylphosphine oxide coupling reaction, trichlorosilane hydrogen reduction, and then use Diphenylphosphine oxide coupling reaction, reduction of trichlorosilane hydrogen, the reaction route is long, in which highly volatile and highly toxic trichlorosilane hydrogen is used, which requires high production equipment, and the products need to be purified by silica gel column chromatography , unable to meet the needs of industrial applications

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