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Metal Cu (I) complex, preparation method and application thereof

A complex and metal technology, applied in organic compound/hydride/coordination complex catalysts, copper organic compounds, chemical instruments and methods, etc. The effect of low preparation cost and mild reaction conditions

Inactive Publication Date: 2016-12-21
SHANXI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The hydroboration reaction of alkynes has attracted widespread attention as an efficient method for preparing alkenyl boron reagents. In the past, this reaction was mainly catalyzed by toxic noble metals. However, toxic noble metals are easy to remain in drug synthesis, which will cause toxic side effects of drugs. Therefore, the invention of a copper catalyst with high efficiency, environmental friendliness and mild conditions can avoid the toxic and side effects of drugs

Method used

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  • Metal Cu (I) complex, preparation method and application thereof
  • Metal Cu (I) complex, preparation method and application thereof
  • Metal Cu (I) complex, preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0044] Embodiment 1: the preparation of metal Cu (I) complex (catalyst) A and B

[0045] 1) Dissolve 0.2mmol (NHC) CuCl in 3ml dry THF in a 20ml dry glass bottle to form a suspension, then put the glass bottle into a glove box refrigerator and freeze at -35°C for 1h;

[0046] 2) In another 20ml dry glass bottle, 42.3mg (0.95eq) [ t Bu 3 PN]Li was dissolved in 3ml of dry THF, and then the glass bottle was placed in a glove box refrigerator and frozen at -35°C for 1h;

[0047] 3) Put 2) the cold [ t Bu 3 PN]Li solution was slowly added dropwise to the cold (NHC) CuCl suspension in 1) under stirring, and continued to stir in the glove box at room temperature for 13h after the dropwise addition;

[0048] 4) After the reaction is complete, dry the solvent (THF) under vacuum to obtain an oily liquid residue, then add 7ml of n-pentane or n-hexane to obtain a suspension, and stir at room temperature for 15min, then pass through neutral diatomaceous earth for a short time Pad filt...

Embodiment 2

[0053] Example 2: Complex B was used to catalyze the hydroboration reaction of phenylacetylene compounds to obtain product 2a with a yield of 89%.

[0054]

Embodiment 3

[0055] Example 3: Complex B was used to catalyze the hydroboration reaction of p-chlorophenylacetylene to obtain product 2b with a yield of 99%.

[0056]

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PUM

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Abstract

The invention provides a metal Cu (I) complex, a preparation method and an application thereof. Tri-tert-butylphosphine imine anions and n-heterocyclic carbine are used as the ligands and coordinated with metal Cu (I) to synthesize the metal Cu (I) complex which can be used for catalyzing the boron hydrogenation reaction of alkyne. The metal Cu is cheap, the complex has relatively high solubility in a hydrocarbon solvent, the reaction conditions required by the catalytic reaction are mild, the reaction yield is relatively high, and the reaction has a specific regio-and stereo-selectivity. The catalyst is low in preparation cost and high in catalytic efficiency, and has a potential large-scale application prospect.

Description

Technical field: [0001] The invention relates to a metal-organic complex, in particular to a metal Cu(I) complex and a preparation method thereof, and the application of the complex as a catalyst in the hydroboration reaction of alkynes. Background technique: [0002] As an important organic intermediate, alkenyl boron reagents can further undergo reactions to form C-C bonds and C-X bonds, such as Suzuki-Miyaura cross-coupling reactions, B(boron)-Heck type reactions, and these reactions can be used in pharmaceuticals Synthesis. The hydroboration reaction of alkynes has attracted widespread attention as an efficient method for the preparation of alkenyl boron reagents. In the past, this reaction was mainly catalyzed by toxic noble metals. However, toxic noble metals are easy to remain in drug synthesis, which will cause toxic side effects of drugs. Therefore, the invention of a copper catalyst with high efficiency, environmental friendliness and mild conditions can avoid the...

Claims

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Application Information

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IPC IPC(8): C07F1/08B01J31/22
CPCB01J31/2273B01J2231/323C07F1/08
Inventor 白涛杨燕辉
Owner SHANXI UNIV