# US 12,766,498 B2 · Platform for the recovery of transition metal catalysts

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- Number: US 12,766,498 B2
- Document ID: US12766498B2
- Status: Granted
- Kind: B2
- Application number: 18/161,048
- Filed: 2023-01-28
- Published: 2023-08-03
- Granted: 2026-10-20
- Earliest claimed: 2022-01-28
- Assignees: Texas Tech University System
- Applicants: Texas Tech University System
- Inventors: Michael Findlater; Guigen Li
- Web page: https://patentgrep.com/patent/US12766498B2

## CPC

- B01J 38/68: including substantial dissolution or chemical precipitation of a catalyst component in the ultimate reconstitution of the catalyst
- B01J: CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS

## Abstract

The present invention includes compositions and methods of using a molecule of Formula I: wherein R is selected from methyl, ethyl, propyl, isopropyl, butyl, phenyl, cyclohexyl, fluoro, chloro, methoxy, ethoxy, butoxy, phenoxy, aryl, alkene, alkyne, and heterocyclic. The molecule of Formula I is a ligand until a metal is added, at which time the molecule is a catalyst.

## Claims

### Claim 1

A molecule of Formula I is a ligand (L):
wherein R is selected from methyl, ethyl, propyl, isopropyl, butyl, cyclohexyl, fluoro, chloro, methoxy, ethoxy, butoxy, phenoxy, aryl, alkene, alkyne, and heterocyclic,
wherein a catalyst is selected for an isomerization reaction catalyst, a hydrosilylation reaction catalyst, a Suzuki-Miyaura coupling catalyst, a Negishi coupling catalyst, a Sonogashira coupling catalyst or a Heck coupling catalyst; and
wherein if the molecule is:
then R is not isopropyl.

### Claim 2 (depends on 1)

The molecule of claim 1, the molecule of Formula I is compound 1:
wherein R is not isopropyl that is synthesized by

### Claim 3 (depends on 2)

The molecule of claim 2, the molecule of compound 1 is a ligand made by:

### Claim 4 (depends on 2)

The molecule of claim 2, wherein the molecule of compound 1 has R selected from benzyl, O-methylbenzyl, trifluorobenzyl, or 2,4,6-methyl benzyl.

### Claim 5 (depends on 1)

The molecule of claim 1, wherein the molecule of Formula I recycles one or more transition metals selected from at least one of: 1st-row transition metals, 2nd-row transition metals, 3rd-row transition metals, main group metals, lanthanide series transition metals, and actinide series transition metals.

### Claim 6 (depends on 1)

The molecule of claim 1, wherein the molecule of Formula I recycles one or more transition metals selected from at least one of: platinum, palladium, vanadium, manganese, iron, cobalt, nickel, copper, zinc, zirconium, ruthenium, iridium, rhodium, hafnium.

### Claim 7 (depends on 1)

The molecule of claim 1, wherein a substrate/product is:
wherein R and X are selected from:

### Claim 8

A method for recycling transition metal catalysis comprising:
combining reactants in a solvent in the presence of a molecule having the formula I is a ligand (L):
wherein R is selected from methyl, ethyl, propyl, isopropyl, butyl, cyclohexyl, fluoro, chloro, methoxy, ethoxy, butoxy, phenoxy, aryl, alkene, alkyne, and heterocyclic;
wherein the catalyst is selected for an isomerization reaction catalyst, a hydrosilylation reaction catalyst, a Suzuki-Miyaura coupling catalyst, a Negishi coupling catalyst, a Sonogashira coupling catalyst or a Heck coupling catalyst; and
wherein if the molecule is:
then R is not isopropyl;
under conditions that catalyze a reaction; and
recycling the molecule of Formula I.

### Claim 9 (depends on 8)

The method of claim 8, wherein the molecule of Formula I is:
wherein R is not isopropyl that is synthesized by

### Claim 10 (depends on 8)

The method of claim 8, wherein the molecule of Formula I is converted into a recyclable catalyst by:

### Claim 11 (depends on 8)

The method of claim 8, wherein R is selected from benzyl, O-methylbenzyl, trifluorobenzyl, or 2,4,6-methyl benzyl.

### Claim 12 (depends on 8)

The method of claim 8, wherein the molecule of Formula I recycles transition metals selected from at least one of: 1st-row transition metals, 2nd-row transition metals, 3rd-row transition metals, main group metals, lanthanide series transition metals, and actinide series transition metals.

### Claim 13 (depends on 8)

The method of claim 8, wherein the molecule of Formula I recycles transition metals selected from at least one of: platinum, palladium, vanadium, manganese, iron, cobalt, nickel, copper, zinc, zirconium, ruthenium, iridium, rhodium, hafnium.

### Claim 14 (depends on 8)

The method of claim 8, wherein a substrate/product is:
wherein R and X are selected from:

### Claim 15 (depends on 8)

The method of claim 8, wherein the reaction is an isomerization reaction, a hydrosilylation reaction, a Suzuki-Miyaura coupling, a Negishi coupling, a Sonogashira coupling or a Heck coupling.

### Claim 16

A tunable tridentate ligand for recyclable homogeneous transition metal catalyst comprising a molecule of Formula I is a ligand (L):
wherein R is selected from methyl, ethyl, propyl, isopropyl, butyl, cyclohexyl, fluoro, chloro, methoxy, ethoxy, butoxy, phenoxy, aryl, alkene, alkyne, and heterocyclic;
wherein the catalyst is selected for an isomerization reaction catalyst, a hydrosilylation reaction catalyst, a Suzuki-Miyaura coupling catalyst, a Negishi coupling catalyst, a Sonogashira coupling catalyst or a Heck coupling catalyst; and
wherein if the molecule is:
then R is not isopropyl.

### Claim 17 (depends on 16)

The tunable tridentate ligand of claim 16, wherein the molecule of Formula I is
wherein R is not isopropyl that is, and is synthesized by:

### Claim 18 (depends on 17)

The tunable tridentate ligand of claim 17, wherein the molecule of Formula I is converted into a recyclable catalyst by:

### Claim 19 (depends on 16)

The tunable tridentate ligand of claim 16, wherein R is selected from benzyl, O-methylbenzyl, trifluorobenzyl, or 2,4,6-methyl benzyl.

### Claim 20 (depends on 16)

The tunable tridentate ligand of claim 16, wherein the molecule of Formula I recycles transition metals selected from at least one of: 1st-row transition metals, 2nd-row transition metals, 3rd-row transition metals, main group metals, lanthanide series transition metals, and actinide series transition metals.

### Claim 21 (depends on 16)

The tunable tridentate ligand of claim 16, wherein the molecule of Formula I recycles transition metals selected from at least one of: platinum, palladium, vanadium, manganese, iron, cobalt, nickel, copper, zinc, zirconium, ruthenium, iridium, rhodium, hafnium.

### Claim 22 (depends on 16)

The tunable tridentate ligand of claim 16, wherein a substrate/product is:
wherein R and X are selected from: