5,5'-position connected 1,1'-biphenyl axis chirality diphosphine ligand and synthetic method thereof

Abstract

A 1,1'-biphenyl-type axial chiral bisphosphine ligand connected at the 5,5' position and a synthesis method thereof in the field of chemical technology. The structural formula of the present invention is as follows: In the formula: R1=hydrogen, fluorine, chlorine, bromine, iodine, trifluoromethyl, the alkyl group of 1-8 carbon or the alkoxy group of 1-8 carbon; R2=hydrogen, fluorine, chlorine, Bromine, iodine, trifluoromethyl, 1-8 carbon alkyl or 1-8 carbon alkoxy; R3 = hydrogen, fluorine, chlorine, bromine, iodine, trifluoromethyl, 1-8 carbon alkyl Or 1-8 carbon alkoxy; R4=hydrogen, fluorine, chlorine, bromine, iodine, trifluoromethyl, 1-8 carbon alkyl or 1-8 carbon alkoxy; R5=hydrogen, fluorine, Chlorine, bromine, iodine, trifluoromethyl, 1-8 carbon alkyl or 1-8 carbon alkoxy; R6=(CH2)n#-[1] (where n1≥5), (CH2)n #-[2]Ph(CH2)n#-[3] (wherein n2, n3≥1), CH2[(CH2)n#-[4]O]n5CH2 (wherein n4, n5≥2). This kind of ligand can be applied to asymmetric reactions catalyzed by various metals, and has high reactivity and stereoselectivity.

Description

technical field [0001] The invention relates to a compound in the technical field of chemical industry and a synthesis method thereof, in particular to a 1,1'-biphenyl-type axial chiral bisphosphine ligand connected at the 5,5' position and a synthesis method thereof. Background technique [0002] The key to asymmetric catalytic synthesis is how to design and synthesize chiral catalysts with high selectivity and catalytic activity, in which chiral ligands are the source of asymmetric induction and control of catalysts. C 2 Chiral bisphosphine ligands, due to their special structure, are widely used in metal-catalyzed asymmetric hydrogenation reactions, such as asymmetric catalytic hydrogenation of ketones, asymmetric catalytic hydrogenation of alkenes and so on. After 30 years of development, a large number of bisphosphine ligands have emerged. After years of research, the axial chiral bisphosphine ligand BINAP containing the binaphthyl structure has been successfully appl...

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Problems solved by technology

[0003] Through literature search to the prior art, it is found that the Synthesis and Molecular Modeling Studies of SYNPHOS published by Jean-Pierre Gene^t in "Eur.J.Org.Chem." (European Organic Chemistry) 2003, pp.1931-1941, a New, Efficient Diphosphane Ligand For Ruthenium-Catalyzed Asymmetric Hydrogenation" (Synthesis and Molecular Modeling of a New and Effective Diphosphine Ligand SYNPHOS in Ruthenium-Catalyzed Asymmetric Hydrogenation), the design of the axial chiral ligand proposed in this paper The concept is to add two larger groups to the ortho position of the biaryl axis, and obtain stable axial chirality through their steric hindrance, but also limit the angle that the biphenyl can rotate, that is, limit the biaryl axis dihedral angle

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