Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

Method for catalyzing intermolecular hydroamination reaction of alkyne and amine

An intermolecular, hydroamination technology, applied in chemical instruments and methods, preparation of organic compounds, preparation of amino compounds by condensation/addition reactions, etc. The effect of mild reaction conditions, simple operation and high yield

Active Publication Date: 2017-11-24
SUZHOU UNIV
View PDF1 Cites 3 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although some metal compounds do show good catalytic activity, they generally have the disadvantages of cumbersome synthesis, low stability and complicated operation.

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
  • Method for catalyzing intermolecular hydroamination reaction of alkyne and amine
  • Method for catalyzing intermolecular hydroamination reaction of alkyne and amine
  • Method for catalyzing intermolecular hydroamination reaction of alkyne and amine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] The present embodiment provides a kind of utilization 15mol% B (C 6 f 5 ) 3 The method for catalyzing the intermolecular hydroamination reaction of phenylacetylene and aniline under the condition of 100 DEG C, the specific steps are as follows:

[0036] 39mg (0.075mmol) of B (C 6 f 5 ) 3 Dissolve in 2mL of chlorobenzene, add 0.22mL (2.0mmol) phenylacetylene and 0.046mL (0.5mmol) aniline to the solution after the reaction is complete, seal the tube, under the conditions of anhydrous, anaerobic and argon protection, 100 Under the condition of ℃, react for 24h. Open the bottle after the reaction temperature is down to room temperature, add 60mg (1.5mmol) LiAlH in the reaction bottle 4 , reacted at 70°C for 2h, quenched the reaction with 2M NaOH, suction filtered, separated, took the organic phase, concentrated it and adsorbed it with basic alumina, and column chromatography (ethyl acetate / petroleum ether=1 / 100 ), to obtain the target product 97mg, yield 99%. The st...

Embodiment 2

[0039] The present embodiment provides a kind of utilization 20mol%B (C 6 f 5 ) 3 The method for catalyzing the intermolecular hydroamination reaction of phenylacetylene and aniline under the condition of 100 DEG C, the specific steps are as follows:

[0040] 51mg (0.1mmol) of B (C 6 f 5 ) 3 Dissolve in 2mL of chlorobenzene, add 0.22mL (2.0mmol) phenylacetylene and 0.046mL (0.5mmol) aniline to the solution after the reaction is complete, seal the tube, under the conditions of anhydrous, anaerobic and argon protection, 100 Under the condition of ℃, react for 12h. Open the bottle after the reaction temperature is down to room temperature, add 60mg (1.5mmol) LiAlH in the reaction bottle 4 , reacted at 70°C for 2h, quenched the reaction with 2M NaOH, suction filtered, separated, took the organic phase, concentrated it and adsorbed it with basic alumina, and column chromatography (ethyl acetate / petroleum ether=1 / 100 ), to obtain the target product 95mg, yield 97%. The struc...

Embodiment 3

[0048] The present embodiment provides a kind of utilization 15mol% B (C 6 f 5 ) 3 The method for catalyzing the intermolecular hydroamination reaction of p-methylphenylacetylene and aniline under the condition of 100 DEG C, the specific steps are as follows:

[0049] 39mg (0.075mmol) of B (C 6 f 5 ) 3 Dissolve in 2mL of chlorobenzene, add 0.25mL (2.0mmol) p-tolueneacetylene and 0.046mL (0.5mmol) aniline to the solution after the reaction is complete, seal the tube, and use the conditions of anhydrous, anaerobic and argon protection Under the condition of 100°C, react for 12h. Open the bottle after the reaction temperature is down to room temperature, add 60mg (1.5mmol) LiAlH in the reaction bottle 4 , reacted at 70°C for 2h, quenched the reaction with 2M NaOH, suction filtered, separated, took the organic phase, concentrated it and adsorbed it with basic alumina, and column chromatography (ethyl acetate / petroleum ether=1 / 100 ), to obtain the target product 100mg, yield...

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 relates to a method for catalyzing intermolecular hydroamination reaction of alkyne and amine. The method comprises the following steps: reacting a terminal alkyne as shown in a formula (1) and a primary aromatic amine as shown in a formula (2) in an aprotic polar solvent at 25-100 DEG C for 6-24 hours under catalysis of tris(pentafluorophenyl)borane and under airtight conditions containing protective atmosphere, wherein structural formulae of the formula (1) and the formula (2) are as shown in the specification, wherein R1 is selected from C1-10 alkyl and aryl; and R2 is selected from hydrogen, C1-10 alkyl, alkoxy, cyano, trifluoromethyl, nitro, halogen and amino. The method is simple and available in raw material, simple in operation, relatively mild in reaction condition, relatively high in yield and relatively wide in application range of a substrate.

Description

technical field [0001] The invention relates to the field of organic chemistry, in particular to a method for catalyzing the intermolecular hydroamination reaction of alkynes and amines. Background technique [0002] Carbon-nitrogen bond is a very important chemical bond, which widely exists in fine chemicals and pharmaceutical intermediates. At the same time, compounds containing carbon-nitrogen bonds can also be used as ligands in the synthesis of metal-organic compounds and in homogeneous catalytic reactions. Therefore, developing efficient methods for constructing carbon-nitrogen bonds is one of the most extensive research contents in organic chemistry, which has important theoretical significance and potential application value. [0003] Amines can be synthesized by nucleophilic substitution reactions between halogenated hydrocarbons and primary or secondary amines, reduction reactions of nitro, amide, azide, and nitrile groups, and Hofmann rearrangement reactions. Co...

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 Applications(China)
IPC IPC(8): C07C209/70C07C211/45C07C211/52
CPCC07C209/60C07C209/70C07C211/45C07C211/52
Inventor 袁丹孙秋贾明森
Owner SUZHOU UNIV
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com