Bis(aminophenylphenol) ligands and transition metal catalysts prepared therefrom

Patent metadata

Field	Value
Publication number	US-10696641-B2
Application number	US-201615569812-A
Country	US
Kind code	B2
Filing date	Apr 25, 2016
Priority date	Apr 27, 2015
Publication date	Jun 30, 2020
Grant date	Jun 30, 2020

Abstract

Disclosed are novel bis(aminophenylphenol) ligands and transition metal compounds derived therefrom. Also disclosed are methods of making the ligands and transition metal compounds.

First claim

What is claimed is:

1. A bis(aminophenylphenol) ligand of formula (III):

wherein:
A is —(CH 2 ) 2 —;
E is —(CH 2 ) 2 — or —(CH 2 ) 3 —;
R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 , R 15 and R 16 are each independently hydrogen, halogen, hydrocarbyl, heteroatom-containing hydrocarbyl, alkoxy, aryloxy, alkylthio, arylthio, BZ 1 Z 2 , N(alkyl) 2 , or SiZ 1 Z 2 Z 3 , wherein the hydrocarbyl is optionally substituted with one or more substituents independently selected from the group consisting of halogen, amino, hydroxy, alkoxy, alkylthio, phosphino, and SiZ 1 Z 2 Z 3 ; and
Z 1 , Z 2 and Z 3 are each independently hydrogen, alkyl, heteroatom-containing alkyl, alkenyl, heteroatom-containing alkenyl, alkynyl, heteroatom-containing alkynyl, amino, alkoxy, aryloxy, aryl, or heteroaryl, wherein the alkyl, heteroatom-containing alkyl, alkenyl, heteroatom-containing alkenyl, alkynyl, heteroatom-containing alkynyl, amino, alkoxy, aryloxy, aryl, or heteroaryl are each optionally and independently substituted with one or more substituents independently selected from the group consisting of halogen, amino, hydroxy, alkoxy, alkylthio, phosphino, and SiZ 1 Z 2 Z 3 ;
where each of Z 1 , Z 2 , and Z 3 of the substituent SiZ 1 Z 2 Z 3 is independently hydride, alkyl, heteroatom-containing alkyl, alkenyl, heteroatom-containing alkenyl, alkynyl, heteroatom-containing alkynyl, amino, alkoxy, aryloxy, aryl, or heteroaryl, wherein the alkyl, heteroatom-containing alkyl, alkenyl, heteroatom-containing alkenyl, alkynyl, heteroatom-containing alkynyl, amino, alkoxy, aryloxy, aryl, or heteroaryl are each optionally and independently substituted with one or more substituents independently selected from the group consisting of halogen, amino, hydroxy, alkoxy, alkylthio, and phosphino;

with the proviso that none of R 1 , R 2 , R 3 , R 4 , R 5 , R 9 , R 10 , R 11 , R 12 and R 13 comprise fluorine.

2. The bis(aminophenylphenol) ligand according to claim 1 , wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 , R 15 and R 16 are each independently hydrogen, halogen, alkyl, heteroatom-containing alkyl, alkoxy, aryloxy, alkylthio, arylthio, N(alkyl) 2 , or SiZ 1 Z 2 Z 3 , wherein the alkyl is optionally substituted.

3. A method for preparing a bis(aminophenylphenol) ligand of formula (III):

wherein:
A is —(CH 2 ) 2 —;
E is —(CH 2 ) 2 — or —(CH 2 ) 3 —;
R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 , R 15 and R 16 are each independently hydrogen, halogen, hydrocarbyl, heteroatom-containing hydrocarbyl, alkoxy, aryloxy, alkylthio, arylthio, BZ 1 Z 2 , N(alkyl) 2 , or SiZ 1 Z 2 Z 3 , wherein the hydrocarbyl is optionally substituted with one or more substituents independently selected from the group consisting of halogen, amino, hydroxy, alkoxy, alkylthio, phosphino, and SiZ 1 Z 2 Z 3 ; and
Z 1 , Z 2 and Z 3 are each independently hydrogen, alkyl, heteroatom-containing alkyl, alkenyl, heteroatom-containing alkenyl, alkynyl, heteroatom-containing alkynyl, amino, alkoxy, aryloxy, aryl, or heteroaryl, wherein the alkyl, heteroatom-containing alkyl, alkenyl, heteroatom-containing alkenyl, alkynyl, heteroatom-containing alkynyl, amino, alkoxy, aryloxy, aryl, or heteroaryl are each optionally and independently substituted with one or more substituents independently selected from the group consisting of halogen, amino, hydroxy, alkoxy, alkylthio, phosphino, and SiZ 1 Z 2 Z 3 ;
where each of Z 1 , Z 2 , and Z 3 of the substituent SiZ 1 Z 2 Z 3 is independently hydride, alkyl, heteroatom-containing alkyl, alkenyl, heteroatom-containing alkenyl, alkynyl, heteroatom-containing alkynyl, amino, alkoxy, aryloxy, aryl, or heteroaryl, wherein the alkyl, heteroatom-containing alkyl, alkenyl, heteroatom-containing alkenyl, alkynyl, heteroatom-containing alkynyl, amino, alkoxy, aryloxy, aryl, or heteroaryl are each optionally and independently substituted with one or more substituents independently selected from the group consisting of halogen, amino, hydroxy, alkoxy, alkylthio, and phosphino;

with the proviso that none of R 1 , R 2 , R 3 , R 4 , R 5 , R 9 , R 10 , R 11 , R 12 and R 13 comprise fluorine;
wherein the method comprises the step of:
reacting a compound of formula (VI):

wherein:
R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 and R 9 are each independently hydrogen, halogen, hydrocarbyl, heteroatom-containing hydrocarbyl, alkoxy, aryloxy, alkylthio, arylthio, BZ 1 Z 2 , N(alkyl) 2 , or SiZ 1 Z 2 Z 3 , wherein the hydrocarbyl is optionally substituted with one or more substituents independently selected from the group consisting of halogen, amino, hydroxy, alkoxy, alkylthio, phosphino, and SiZ 1 Z 2 Z 3 ; and
Z 1 , Z 2 and Z 3 are each independently hydrogen, alkyl, heteroatom-containing alkyl, alkenyl, heteroatom-containing alkenyl, alkynyl, heteroatom-containing alkynyl, amino, alkoxy, aryloxy, aryl, or heteroaryl, wherein the alkyl, heteroatom-containing alkyl, alkenyl, heteroatom-containing alkenyl, alkynyl, heteroatom-containing alkynyl, amino, alkoxy, aryloxy, aryl, or heteroaryl are each optionally and independently substituted with one or more substituents independently selected from the group consisting of halogen, amino, hydroxy, alkoxy, alkylthio, phosphino, and SiZ 1 Z 2 Z 3 ;
where each of Z 1 , Z 2 , and Z 3 of the substituent SiZ 1 Z 2 Z 3 is independently hydride, alkyl, heteroatom-containing alkyl, alkenyl, heteroatom-containing alkenyl, alkynyl, heteroatom-containing alkynyl, amino, alkoxy, aryloxy, aryl, or heteroaryl, wherein the alkyl, heteroatom-containing alkyl, alkenyl, heteroatom-containing alkenyl, alkynyl, heteroatom-containing alkynyl, amino, alkoxy, aryloxy, aryl, or heteroaryl are each optionally and independently substituted with one or more substituents independently selected from the group consisting of halogen, amino, hydroxy, alkoxy, alkylthio, and phosphino;

with the proviso that none of R 1 , R 2 , R 3 , R 4 , R 5 , R 9 , R 10 , R 11 , R 12 and R 13 comprise fluorine;
with a compound of formula (VII):

wherein:
A is —(CH 2 ) 2 —; and
E is —(CH 2 ) 2 — or —(CH 2 ) 3 —;

in the presence of formaldehyde, to yield the bis(aminophenylphenol) ligand of formula (III) above.

Assignees

• Univation Tech Llc

Inventors

• Faler Catherine Anne
• Ramirez Kevin P

Classifications

• C07D295/096

  with the ring nitrogen atoms and the oxygen or sulfur atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings · CPC title

• B01J31/2243

  At least one oxygen and one nitrogen atom present as complexing atoms in an at least bidentate or bridging ligand · CPC title

• B01J2531/0258

  Flexible ligands, e.g. mainly sp3-carbon framework as exemplified by the "tedicyp" ligand, i.e. cis-cis-cis-1,2,3,4-tetrakis(diphenylphosphinomethyl)cyclopentane · CPC title

• B01J31/143

  of aluminium · CPC title

• B01J2531/48

  Zirconium · CPC title