Imines with tunable nucleophilicity and steric properties through metal coordination: applications as ligands and metalloorganocatalysts

Patent metadata

Field	Value
Publication number	US-10399072-B2
Application number	US-201515510119-A
Country	US
Kind code	B2
Filing date	Sep 9, 2015
Priority date	Sep 11, 2014
Publication date	Sep 3, 2019
Grant date	Sep 3, 2019

Abstract

The invention describes phospho-amino pincer-type ligands, metal complexes thereof, and catalytic methods comprising such metal complexes for conversion of carbon dioxide to methanol, conversion of aldehydes into alcohols, conversion of aldehydes in the presence of a trifluoromethylation agent into trifluorinated secondary alcohols, cycloaddition of carbon dioxide to an epoxide to provide cyclic carbonates or preparation of an amide from the combination of an alcohol and an amine.

First claim

What is claimed is:

1. A compound comprising formula (II):

wherein R 1 , R 2 , R 3 , and R 4 are each independently an unsubstituted alkyl group having between one and twelve carbon atoms, an unsubstituted aryl group having between one and twelve carbon atoms, an unsubstituted aralkyl group having between one and twelve carbon atoms, or any of these groups substituted with amino, hydroxyl, or alkoxyl;
R 5 is a hydrogen atom or an unsubstituted alkyl, an unsubstituted aryl, an unsubstituted aralkyl group having between one and twelve carbon atoms, or any of these groups substituted with amino, hydroxyl, or alkoxyl;
each Z, independently, is CR 6 ;
R 6 is a hydrogen atom or an unsubstituted alkyl group having between one and twelve carbon atoms, an unsubstituted aryl group having between one and twelve carbon atoms, an unsubstituted aralkyl group having between one and twelve carbon atoms, or any of these groups substituted with amino, hydroxyl, or alkoxyl;
D is CR 9 R 10 ;
R 9 and R 10 are each independently a hydrogen, an unsubstituted alkyl group having between one and twelve carbon atoms, an unsubstituted aryl group having between one and twelve carbon atoms, or an unsubstituted aralkyl group having between one and twelve carbon atoms, or any of these groups substituted with amino, hydroxyl, or alkoxyl;
M is nickel (Ni), a nickel ion or a nickel salt; and
X is a halide or a hydrogen atom.

2. The compound of claim 1 , wherein R 1 , R 2 , R 3 , and R 4 are each an alkyl, each alkyl group having two to ten carbon atoms, each Z is CH and R 5 is a hydrogen atom.

3. The compound of claim 2 , wherein R 1 , R 2 , R 3 , and R 4 are each a four carbon alkyl group.

4. The compound of claim 1 , wherein X is a hydride.

5. The compound of claim 1 , wherein X is a halide.

Assignees

• Univ King Abdullah Sci & Tech

Inventors

• Huang Kuo-Wei
• Zhao Qianyi

Classifications

• B01J2531/0244

  Pincer-type complexes, i.e. consisting of a tridentate skeleton bound to a metal, e.g. by one to three metal-carbon sigma-bonds · CPC title

• B01J2231/763

  of -CH-XH (X= O, NH/N, S) to -C=X or -CX triple bond species · CPC title

• B01J2231/625

  of CO2 · CPC title

• B01J2231/341

  1,2-additions, e.g. aldol or Knoevenagel condensations · CPC title

• B01J31/2295

  Cyclic compounds, e.g. cyclopentadienyls · CPC title