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Supported cluster catalyst and preparation and application thereof

A catalyst and supported technology, applied in the preparation of carbon-based compounds, the preparation of organic compounds, physical/chemical process catalysts, etc., can solve the problems of large substrate limitations, large catalyst dosage, long reaction time, etc., and achieve utilization High, simple synthesis method, mild reaction conditions

Active Publication Date: 2019-11-05
ANHUI UNIVERSITY +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, these catalyst systems still have disadvantages such as excess alkyne, long reaction time, large amount of catalyst, large substrate limitation, and low yield.

Method used

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  • Supported cluster catalyst and preparation and application thereof
  • Supported cluster catalyst and preparation and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Example 1: Au 12 Ag 32 / ZnO catalyzed the reaction of phenylacetylene with 2,2,2,-trifluoroacetophenone in DMSO solution.

[0030] Au 12 Ag 32 / ZnO catalyst (30mg), phenylacetylene (0.5mmol), 2,2,2,-trifluoroacetophenone (0.75mmol), K 2 CO 3 (0.24mmol) and DMSO (500μL) were added into a dry Schlenk flask, under the protection of argon, the reaction mixture was stirred at 50°C for 12h, and the reaction solution and solid catalyst were separated by centrifugation. Extract the target product in the reaction solution with saturated brine and dichloromethane, collect CH 2 Cl 2 anhydrous Na 2 SO 4 After drying, the crude product was purified by silica gel column chromatography (EtOAc / PE=1:20) to give the main product in 87.7% yield.

[0031] 1 H NMR (400MHz, CDCl 3 )δ7.83~7.81(m,2H),7.53(d,J=8.0Hz,2H),7.45~7.34(m,6H), 3.13(s,1H)ppm; 13 C NMR (101MHz, CDCl 3 )δ134.26, 131.04, 128.53, 127.45, 127.23, 126.17, 123.78, 120.94, 119.92, 87.04, 83.40, 72.32ppm.

Embodiment 2

[0032] Example 2: Au 12 Ag 32 / ZnO catalyzed the reaction of phenylacetylene with 2,2,2,-trifluoroacetophenone in DMF solution.

[0033] Au 12 Ag 32 / ZnO catalyst (30mg), phenylacetylene (0.5mmol), 2,2,2,-trifluoroacetophenone (0.75mmol), K 2 CO 3 (0.24mmol) and DMF (500μL) were added into a dry Schlenk flask, under the protection of argon, the reaction mixture was stirred at 50°C for 12h, and the reaction solution and solid catalyst were separated by centrifugation. Extract the target product in the reaction solution with saturated brine and dichloromethane, collect CH 2 Cl 2 anhydrous Na 2 SO 4 After drying, the crude product was purified by silica gel column chromatography (EtOAc / PE=1:20) to give the main product in 96.7% yield.

Embodiment 3

[0034] Example 3: Au 12 Ag 32 / ZnO catalyzed the reaction of phenylacetylene with 2,2,2,-trifluoroacetophenone in acetonitrile solution.

[0035] Au 12 Ag 32 / ZnO catalyst (30mg), phenylacetylene (0.5mmol), 2,2,2,-trifluoroacetophenone (0.75mmol), K 2 CO 3 (0.24mmol) and acetonitrile (500μL) were added into a dry Schlenk flask, under the protection of argon, the reaction mixture was stirred at 50°C for 12h, and the reaction solution and solid catalyst were separated by centrifugation. The solvent in the reaction solution was removed by a rotary evaporator, and the crude product was purified by silica gel column chromatography (EtOAc / PE=1:20) to obtain the main product with a yield of 19.7%.

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PUM

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Abstract

The invention discloses a supported cluster catalyst and preparation and application thereof. The molecular formula of the supported cluster catalyst is Au1Ag24 / ZnO or Au12Ag32 / ZnO, wherein the molecular formula of a Au1Ag24 cluster is Au1Ag24(SPhMe2)18(PPh4) which is called Au1Ag24 for short; the molecular formula of a Au12Ag32 cluster is Au12Ag32(SPhF2)30(PPh4)4 which is called Au12Ag32 for short. The Au1Ag24 / ZnO catalyst and the Au12Ag32 / ZnO catalyst can catalyze an alkynylation reaction of trifluoromethyl ketone at high yield, reaction conditions are mild, the catalyst can be recycled at least five times, and the universality of a substrate is high.

Description

technical field [0001] The invention relates to a solid catalyst, in particular to a supported cluster catalyst and its preparation and application. Background technique [0002] Due to the small size and high electronegativity of fluorine atoms, the stability, polarity and lipophilicity of organic compounds containing trifluoromethyl groups are significantly changed. Therefore, compounds containing trifluoromethyl groups have important application value in the fields of new functional materials and pharmacy. Among them, trifluoromethyl propargyl alcohol compounds are important intermediates for the synthesis of complex compounds such as many drugs and natural products. CF 3 The -propargyl alcohol structure exists in various natural products and drugs, such as the anti-HIV drug Efavirenz. The main methods for the synthesis of trifluoromethyl propargyl alcohol compounds include the reduction of alkynyl ketone compounds and the nucleophilic addition of terminal alkynes to k...

Claims

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Application Information

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IPC IPC(8): B01J31/26C07C45/69C07C49/813
CPCB01J31/26C07C45/69C07C49/813Y02P20/584
Inventor 盛鸿婷孙莉莉朱满洲徐三能强泽明陈宝乾
Owner ANHUI UNIVERSITY
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