Zwitterion-ruthenium complex for catalytic aerobic oxidation reactions

Patent metadata

Field	Value
Publication number	US-11298694-B2
Application number	US-202017080256-A
Country	US
Kind code	B2
Filing date	Oct 26, 2020
Priority date	Oct 25, 2019
Publication date	Apr 12, 2022
Grant date	Apr 12, 2022

Abstract

Zwitterion ligand metal complexes and methods of aerobic oxidation using a zwitterion ligand metal complex are provided. The zwitterion ligand metal complexes can include a transition metal salt and a zwitterion ligand, which can comprise a non-conjugated amide anion-phosphonium cation, an amide anion-ammonium cation, or an iminium cation. The methods of aerobic oxidation can include combining the zwitterion ligand metal complex with an oxidizable compound and molecular oxygen to allow the isolation of an oxidized compound from the oxidizable compound.

First claim

We claim:

1. A zwitterion ligand metal complex, comprising:
a transition metal salt; and
a zwitterion ligand of the structure:

2. The zwitterion ligand metal complex according to claim 1 , wherein the metal salt is a ruthenium (III) salt.

3. The zwitterion ligand metal complex according, to claim 2 , wherein the ruthenium (III) salt is RuCl 3 .

4. A method of aerobic oxidation, comprising:
providing the zwitterion ligand metal complex according to claim 1 ;
providing oxidizable compound;
providing molecular oxygen;
combining the zwitterion ligand metal complex, the oxidizable compound, and the molecular oxygen to produce an oxidized compound; and
isolating the oxidized compound from the oxidizable compound.

5. The method according to claim 4 , wherein the oxidizable compound is a primary alcohol, secondary alcohol, a hydroquinone, an indoline, or 1,2,3,4-tetrahydroquinoxaline, wherein the primal), alcohol is an aliphatic alcohol, a benzyl alcohol, or an allyl alcohol, wherein the secondary alcohol is an aliphatic alcohol, a benzyl alcohol, an allyl alcohol, a diphenyl methyl alcohol, a 1-phenyl allyl alcohol, or a 1-alkenyl-allyl alcohol, and wherein the oxidized compound is an aldehyde or a ketone.

6. The method according to claim 4 , further comprising:
providing a solvent; and
combining the solvent with the zwitterion ligand metal complex, the oxidizable compound, and the molecular oxygen.

7. The method according to claim 6 , wherein the solvent is 1,2-dichloroethane (DCE), and wherein providing molecular oxygen comprises providing air.

8. The method according to claim 4 , further comprising heating to a temperature in a range of from 23° C. to 100° C.

Assignees

• Univ Hong Kong Chinese

Inventors

• Hu Rong-Bin
• Lam Ying-Pong
• Ng Wing-Hin
• Yeung Ying-Yeung
• Ke Zhihai

Classifications

• C07C5/09

  to carbon-to-carbon double bonds · CPC title

• B01J31/226 Primary

  Sulfur, e.g. thiocarbamates · CPC title

• C07C2601/18

  with a ring being at least seven-membered · CPC title

• C07C46/08

  with molecular oxygen · CPC title

• B01J2531/004

  Ligands · CPC title