Method for producing perfluoroalkylated compound

Patent metadata

Field	Value
Publication number	US-10995043-B2
Application number	US-201616061449-A
Country	US
Kind code	B2
Filing date	Dec 12, 2016
Priority date	Dec 15, 2015
Publication date	May 4, 2021
Grant date	May 4, 2021

Abstract

Provided is a method for producing a perfluoroalkylated compound at low cost, safely and with high efficiency. A method for producing a perfluoroalkylated compound, comprising reacting a bis(perfluoroalkanoyl) peroxide with a compound having a carbon-carbon unsaturated bond and/or an aromatic ring having a hydrogen atom bonded thereto in the presence of a copper catalyst.

First claim

The invention claimed is:

1. An aziridine derivative represented by formula (V-1):

wherein Rf represents a perfluoroalkyl group having 1 to 6 carbon atoms, R 3 , R 5 and R 6 , which are the same or different, each represent a hydrogen atom or a substituted or unsubstituted C 1-6 -alkyl group, R 5 and R 6 may be linked to form a 5- to 7-membered carbon ring together with CH—C(R 3 )—CH to which they are attached, and R 7 represents a substituted or unsubstituted C 1-6 -alkyl group or a substituted or unsubstituted phenyl group.

2. A method for producing the aziridine derivative according to claim 1 , comprising reacting a bis(perfluoroalkanoyl) peroxide represented by formula (I):
Rf—CO—OO—CO—Rf  (I)

wherein Rf represents a perfluoroalkyl group having 1 to 6 carbon atoms, with a compound represented by formula (IVa):
R 7 —SO 2 —NH—CH(R 6 )—C(R 3 )═CH(R 5 )  (IVa)

wherein R 3 , R 5 , R 6 , and R 7 are as defined in claim 1 , in the presence of a copper catalyst.

3. The method according to claim 2 , wherein the bis(perfluoroalkanoyl) peroxide is produced from perfluoroalkanoic anhydride and a urea-hydrogen peroxide complex.

4. The method according to claim 2 , wherein the copper catalyst is [Cu(CH 3 CN) 4 ]PF 6 .

5. The aziridine derivative according to claim 1 , wherein R 3 , R 5 and R 6 , which are the same or different, each represent a hydrogen atom or a C 1-6 -alkyl group, R 5 and R 6 may be linked to form a 5- to 7-membered carbon ring together with CH—C(R 3 )—CH to which they are attached, and R 7 represents a C 1-6 -alkyl group or a phenyl group, wherein the C 1-6 -alkyl group may be substituted with one or more substituents selected from a halogen atom, a hydroxyl group, an amino group, a mono- or dialkylamino group, a C 1-6 -alkoxy group, an oxo group, an aromatic group, and a heterocyclic group, and the phenyl group may be substituted with one or more substituents selected from a methyl group, a methoxy group, a fluorine atom, a bromine atom, and a nitro group.

6. The aziridine derivative according to claim 1 , wherein R 3 , R 5 and R 6 , which are the same or different, each represent a hydrogen atom or a C 1-6 -alkyl group, R 5 and R 6 may be linked to form a 5- to 7-membered carbon ring together with CH—C(R 3 )—CH to which they are attached, and R 7 represents a C 1-6 -alkyl group, a phenyl group, a tolyl group, a 4-methoxyphenyl group, a 4-fluorophenyl group, a 4-bromophenyl group, or a 4-nitrophenyl group, wherein the C 1-6 -alkyl group may be substituted with one or more substituents selected from a halogen atom, a hydroxyl group, an amino group, a mono- or dialkylamino group, a C 1-6 alkoxy group, an oxo group, an aromatic group, and a heterocyclic group.

Assignees

• Riken

Inventors

• Sodeoka Mikiko
• Kawamura Shintaro

Classifications

• C07D207/444

  having two doubly-bound oxygen atoms directly attached in positions 2 and 5 · CPC title

• C07C67/293

  by isomerisation; by change of size of the carbon skeleton · CPC title

• C07C67/343

  by increase in the number of carbon atoms · CPC title

• C07D279/02

  1,2-Thiazines; Hydrogenated 1,2-thiazines · CPC title

• C07C2603/26

  Phenanthrenes; Hydrogenated phenanthrenes · CPC title