Catalytic manufacturing method for imine having no substituent group on the nitrogen, and use for the imine produced

Patent metadata

Field	Value
Publication number	US-9328069-B2
Application number	US-201314760828-A
Country	US
Kind code	B2
Filing date	Mar 28, 2013
Priority date	Jan 16, 2013
Publication date	May 3, 2016
Grant date	May 3, 2016

Abstract

The present invention relates to a method for manufacturing an imine having no substituent group on the nitrogen by using, as a catalyst, a metal complex on an organic azide compound, and more specifically relates to a method in which a metal-complex catalyst is used to produce, from an organic azide having an alpha-hydrogen, an imine having no substituent group on the nitrogen via a continuous nitrogen removal and 1,2-hydrogen transfer reaction. The imine having no substituent group on the nitrogen manufactured by means of the method of the present invention can synthesize diverse coupling products comprising amine compounds by means of reactions with diverse nucleophiles.

First claim

What is claimed is:

1. A method of synthesizing an imine having no substituent on a nitrogen, comprising:
adding a metal complex to an organic azide.

2. The method according to claim 1 , wherein the metal complex is a ruthenium complex.

3. The method according to claim 2 , wherein the ruthenium complex is a ruthenium complex of Formula 1 or Formula 2:

where R 1 and R 2 are each independently hydrogen, substituted or unsubstituted phenyl, or C 1 ˜C 5 alkyl, and FG is amino, hydroxyl, amide, ester, or ether.

4. The method according to claim 1 , wherein the synthesis is performed through irradiation of visible rays.

5. A method of manufacturing a binding product through addition of the imine manufactured in claim 1 with a nucleophile, wherein the addition is performed under neutral conditions without ammonia.

6. The method according to claim 5 , wherein the binding product is an amine.

7. The method according to claim 5 , wherein the nucleophile is selected from the group consisting of an organic metal compound, an organic carbon compound, and an organic heteroelement compound.

Assignees

• Postech Acad Ind Found

Inventors

• Park Jai Wook
• Rhee Young Ho
• Lee Jin Hee
• Han Jung Hoon
• Gupta Sreya
• Jeong Wook

Classifications

• C07C221/00

  Preparation of compounds containing amino groups and doubly-bound oxygen atoms bound to the same carbon skeleton · CPC title

• C07F7/1892

  by reactions not provided for in C07F7/1876 - C07F7/1888 · CPC title

• B01J31/12

  containing organo-metallic compounds or metal hydrides · CPC title

• C07F15/0046

  Ruthenium compounds · CPC title

• C07C249/02

  of compounds containing imino groups · CPC title