Unlock instant, AI-driven research and patent intelligence for your innovation.

A method for synthesizing α-vinylsilane under heterogeneous conditions

A vinylsilane, heterogeneous technology, applied in the field of synthesizing α-vinylsilane under heterogeneous conditions, can solve the problems of low yield and the like

Active Publication Date: 2021-04-16
GUANGXI NORMAL UNIV
View PDF1 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Recently, Jin Liqun’s group at Zhejiang University of Technology reported the α-regioselective hydrosilation of alkynes catalyzed by NN bidentate ligands, but the yield of α-vinylsilanes for alkyl groups was also very low (Org.Lett .2019, 21, 5767-5772)
Therefore, the challenge of this method is how to effectively control the selectivity of the reaction

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • A method for synthesizing α-vinylsilane under heterogeneous conditions
  • A method for synthesizing α-vinylsilane under heterogeneous conditions
  • A method for synthesizing α-vinylsilane under heterogeneous conditions

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0017] Preparation and characterization of phenyl(1-phenylvinyl)silane:

[0018]

[0019] Under an argon atmosphere, add 15 mg of heterogeneous catalyst, 1.0 mmol of phenylacetylene, 1.2 mmol of phenylsilane and 2 mL of anhydrous tetrahydrofuran into a 25 mL branch tube with a magnetic stirring bar, then add 30 mg of sodium tert-butoxide, and The reaction was stirred at room temperature for 4 hours, the solvent was removed in vacuo, and the crude product was purified by column chromatography using petroleum ether as eluent to obtain a colorless liquid product with a yield of 71%.

[0020] The product is characterized by:

[0021] 1 H NMR (400MHz, CDCl 3 )δ7.51-7.45(m,2H),7.30-7.09(m,8H),6.13(d,J=2.3Hz,1H),5.72(d,J=2.3Hz,1H),4.74(s,2H ). 13 C NMR (100MHz, CDCl 3 ) δ 144.2, 142.3, 135.6, 131.4, 131.2, 129.9, 128.5, 128.09, 127.3, 126.5.

[0022] The synthesis method and characterization data of the heterogeneous catalyst in this example are as follows: add 0.3 mmol 5,5-...

Embodiment 2

[0024] Preparation and characterization of phenyl(1-(p-methylphenyl)vinyl)silane:

[0025]

[0026] Under an argon atmosphere, add 20 mg of the heterogeneous catalyst, 1.0 mmol of 4-methylphenylacetylene, 1.1 mmol of phenylsilane, and 2 mL of anhydrous tetrahydrofuran into a 25 mL branched tube with a magnetic stirrer, followed by 35 mg of tert-butanol Na, and the reaction was stirred at room temperature for 4 hours, the solvent was removed in vacuo, and the crude product was purified by column chromatography using petroleum ether as eluent to obtain a colorless liquid product with a yield of 74%.

[0027] The product is characterized by:

[0028] 1 H NMR (400MHz, CDCl 3 )δ7.79-7.75(m,2H),7.58-7.43(m,5H),7.31-7.24(m,2H),6.40(d,J=2.3Hz,1H),5.97(d,J=2.3Hz ,1H),5.03(s,2H),2.48(s,3H). 13 C NMR (100MHz, CDCl 3 ) δ 143.8, 139.3, 137.00, 135.6, 131.3, 130.4, 129.8, 129.2, 128.1, 126.3, 21.0.

[0029] The synthesis method and characterization data of the heterogeneous catalys...

Embodiment 3

[0031] Preparation and characterization of phenyl(1-(4-methoxyphenyl)vinyl)silane:

[0032]

[0033] Under an argon atmosphere, add 20 mg of the heterogeneous catalyst, 1.0 mmol of 4-methoxyphenylacetylene, 1.1 mmol of phenylsilane, and 1.5 mL of anhydrous tetrahydrofuran into a 25 mL branch tube with a magnetic stir bar, and then add 35 mg of tert- sodium butoxide, and the reaction was stirred at room temperature for 4 hours, the solvent was removed in vacuo, and the crude product was purified by column chromatography using petroleum ether as eluent to obtain a colorless liquid product with a yield of 70%.

[0034] The product is characterized by:

[0035] 1 H NMR (400MHz, CDCl3 )δ7.51-7.45(m,2H),7.30-7.19(m,5H),6.75-6.68(m,2H),6.07(d,J=2.2Hz,1H),5.64(d,J=2.2Hz ,1H),4.73(s,2H),3.64(s,3H). 13 C NMR (100MHz, CDCl 3 ) δ 159.0, 143.1, 135.5, 134.6, 131.3, 129.8, 129.5, 128.1, 127.5, 113.9, 55.2.

[0036] The synthesis method and characterization data of the heterogeneous ...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

The invention discloses a method for synthesizing under heterogeneous conditions α ‑vinylsilane method, this method in hypernuclear clusters [Co 14 ( mu 3 -OH 4 (H 2 dpbt) 6 Cl 12 ] • 23C 6 h 10 O-Catalyzed Synthesis of Alkynes by Highly Chemo, Regio, and Stereoselective Hydrosilylation of Alkynes with Primary and Secondary Silanes α ‑vinylsilane, a high-nuclear cluster catalyst with high selectivity for electron-unbiased alkyl alkynes.

Description

technical field [0001] The chemical synthesis of the present invention is specifically a method for synthesizing α-vinylsilane under heterogeneous conditions. Background technique [0002] Since α-vinylsilane is harmless, highly stable, and easy to handle and store, it is a structural unit that has attracted widespread attention, and is widely used in the synthesis of organic intermediates, the preparation of polymeric silicone materials and fine Synthesis of chemicals (Chem. Soc. Rev. 2010, 39, 4114-4129; Chem. Soc. Rev. 2010, 39, 4114-4129; Chem. Rev. 1995, 95, 1375-1408). Among all the synthesis methods of α-vinylsilanes, the transition metal-catalyzed hydrosilylation of alkynes is a simple and efficient method with 100% atom utilization, but the reaction may produce various by-products, such as β- (Z)-, β-(E)-, α-vinylsilanes and products of overhydrogenation, thereby affecting the efficiency of the process, such as figure 1 Shown, (Angew. Chem., Int. Ed. 2017, 56, 432...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
Patent Type & Authority Patents(China)
IPC IPC(8): C07F7/08C07F7/10C07F7/18B01J31/22
CPCB01J31/1815B01J2231/323B01J2531/845C07F7/0896C07F7/1876
Inventor 贾均松唐海涛黄富平潘英明
Owner GUANGXI NORMAL UNIV