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A kind of β-diimine zinc-lithium double metal compound and its preparation method and application in hydroboration of isocyanate

A technology of zinc diimide and isocyanate, which is applied in the field of β-diimide zinc-lithium bimetallic compound and its preparation, and achieves the effects of high activity, high catalytic efficiency and high yield

Active Publication Date: 2022-02-25
NANJING FORESTRY UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] There are few reports on the catalysis of zinc-lithium double metal halides, and no one has used such catalysts to catalyze the hydroboration of isocyanates.

Method used

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  • A kind of β-diimine zinc-lithium double metal compound and its preparation method and application in hydroboration of isocyanate
  • A kind of β-diimine zinc-lithium double metal compound and its preparation method and application in hydroboration of isocyanate
  • A kind of β-diimine zinc-lithium double metal compound and its preparation method and application in hydroboration of isocyanate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] The preparation of β-diimine zinc lithium double metal compound, the process is as follows:

[0024] (1) Under anhydrous and oxygen-free conditions, in a single-port reaction tube, dissolve the β-diimine ligand in ether solution, add n-butyl lithium dropwise to the above solution at -80~-40°C, and return to room temperature for reaction Overnight, obtain β-diimine ligand lithium salt; Wherein, the molar ratio of β-diimine ligand, n-butyllithium is 1: 1.1;

[0025] (2) Add the above solution dropwise to the ether solution of zinc iodide at -80~-40°C, return to room temperature and react for 8~24 hours to obtain β-diimide zinc-lithium bimetallic compound; among them, β-diimide The molar ratio of imine ligand lithium salt and zinc iodide is 1:1. The product was filtered, and the filtrate was concentrated to about 5 mL, and 1.63 g of colorless crystals were precipitated at 2°C, with a yield of 72%. 1 H NMR (600MHz, C 6 D. 6 ): δ7.13(m, 3H, Ar-H), 6.81(m, 2H, Ar-H), 4.95...

Embodiment 2

[0027] β-diimine zinc lithium double metal compound catalyzes the reaction of isopropyl isocyanate and pinacol borane, the process is as follows:

[0028] Under anhydrous and oxygen-free conditions, add 0.29 μmol β-diimide zinc lithium bismetal compound, 5.88 μmol isopropyl isocyanate and 20.58 μmol pinacol borane to a single-port reaction tube in sequence, and use 0.5 mL C 6 D. 6 Dissolve, add a stirring bar and stir at 60° C. for 6 h, and the yield is 99% according to nuclear magnetic spectrum.

Embodiment 3

[0030] The β-diimine zinc-lithium double metal compound catalyzes the reaction of ethyl isocyanate and pinacol borane, and the process is as follows:

[0031] Under anhydrous and oxygen-free conditions, add 0.29 μmol β-diimide zinc-lithium bimetallic compound, 5.88 μmol ethyl isocyanate and 20.58 μmol pinacol borane to a single-port reaction tube in sequence, and use 0.5 mL C 6 D. 6 Dissolve, add a stirring bar and stir at 60° C. for 6 h, and the yield is 99% according to nuclear magnetic spectrum.

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Abstract

The invention discloses a β-diimine zinc-lithium double metal compound, a preparation method thereof and an application in hydroboration of isocyanate. The hydroboration method of the isocyanate is as follows: under anhydrous and oxygen-free conditions, dissolve the β-diimide zinc-lithium double metal compound in a solvent, add pinacol borane, then add isocyanate, and react at 60 ° C for 6 to 12 hours . In the hydroboration method of isocyanate of the present invention, the β-diimide zinc-lithium bimetallic catalyst has high activity in catalyzing the reaction between isocyanate and pinacol borane, wide substrate universality, and high reaction yield.

Description

technical field [0001] The invention relates to the technical field of hydroboration of isocyanate, in particular to a β-diimine zinc-lithium double metal compound, a preparation method thereof and an application in hydroboration of isocyanate. Background technique [0002] The addition reaction of active hydrogen to unsaturated functional groups has attracted extensive attention in recent years, especially the hydrogenation reaction of carbon-oxygen double bonds has potential application prospects in the fields of materials science and biochemistry. The reduction of unsaturated functional groups is mostly a catalytic reaction involving metals. In the past few decades, there have been a large number of studies on transition metals catalyzing this type of reaction, among which, the research on zinc catalyzed this type of reaction is relatively less. The earliest studies were the catalytic hydrosilation of aldehydes and ketones by Noyori using silane and zinc catalysts (Ohkuma...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F19/00B01J31/22C07C209/00C07C211/06C07C211/05C07C211/03C07C211/38C07C211/47C07C211/45C07C213/02C07C217/84
CPCC07F3/06B01J31/1805C07C209/00C07C213/02C07C2603/74B01J2231/641B01J2531/11B01J2531/26B01J2531/0205B01J2531/0213C07C211/06C07C211/05C07C211/03C07C211/38C07C211/47C07C211/45C07C217/84
Inventor 马猛涛肖钤曹旭郑玉坤
Owner NANJING FORESTRY UNIV
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