Chiral diphosphine ligand-iridium composite nanocatalyst and application thereof to asymmetric hydrogenation synthesis of (S)-metolachlor

Abstract

The invention relates to a chiral diphosphine ligand-iridium composite nanocatalyst and application thereof. The catalysts are prepared by compounding chiral diphosphine ligand-iridium composite catalyst and nanomaterials together; the catalyst is used for catalyzing hydrogenation reaction of 2-methyl-6-ethyl-N-methylene aniline (EMA-imine) to obtain (S)-N-(1-methoxyl-2-propyl)-2-methyl-6-ethyl aniline ((S)-NAA), wherein enantiomeric excess (ee) value can reach 85 percent; the (S)-NAA and chloroacetyl chloride are subjected to acylation reaction to obtain (S)-metolachlor with ee value of 84.5 percent; and the catalyst can be repeatedly used for over 5 times.

Description

technical field [0001] The invention belongs to the technical field of chiral pesticide production. Chiral bisphosphine ligand provided by the invention and iridium-cyclooctadiene complex ([IrCl(cod)] 2 ) and the nano-carrier to obtain the chiral bisphosphine ligand-iridium composite catalyst can be applied to the asymmetric hydrogenation reaction of imine, and then can be used for the production of chiral herbicide (S-) metolachlor. technical background [0002] Metolachlor (trade name: Dual) is a broad-spectrum herbicide developed by the former Ciba-Geigy Company. It is low-toxic to humans and animals and can be used to control annual grass weeds and other crops in corn and other dry fields. Broadleaf weeds. Studies have found that metolachlor has four stereoisomers, one chiral axis and one chiral center, and 95% of the herbicidal activity exists in the (1'S)-diastereomer, and its three-dimensional structural formula is as follows: [0003] [0004] Among the four i...

AI Technical Summary

Problems solved by technology

But the catalyzer of this method is difficult to reuse, so that its cost of use is higher, for this reason, the applicant loads the catalyzer on the nanoparticles on the basis of the aforementioned application, so that the catalyzer can be reused more than 5 times, and the e.e.% is basically not falling

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