# US 11,993,592 B2 · Phebox ligands and methods of making same

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- Number: US 11,993,592 B2
- Document ID: US11993592B2
- Status: Granted
- Kind: B2
- Application number: 17/939,047
- Filed: 2022-09-07
- Published: 2023-01-26
- Granted: 2024-05-28
- Earliest claimed: 2020-03-23
- Assignees: Rutgers, The State University of New Jersey
- Applicants: Rutgers, The State University of New Jersey
- Inventors: Alan S. Goldman; Thomas R. Dugan
- Web page: https://patentgrep.com/patent/US11993592B2

## CPC

- C07D 413/10: linked by a carbon chain containing aromatic rings
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)

## Abstract

The present disclosure provides compounds which are useful for a number of catalytic transformations of organic molecules, non-limiting examples including dehydrogenation of alkanes. The present disclosure further relates to methods of preparing the compounds of the present disclosure.

## Claims

### Claim 1

A method of making the compound of formula (I), or a salt or solvate thereof:
wherein:
R1 and R2 are each CH3, or R1 and R2 taken together are —(CH2)4— or —(CH2)5—;
R3 is selected from the group consisting of CF3, CF2CF3, CN, and NO2;
R4 is selected from the group consisting of CF3, CF2CF3, CN, and NO2; with the provisos that:
if one of R3 and R4 is CN, then the other is CF2CF3 or NO2;
if one of R3 and R4 is NO2, then the other is CF3, CF2CF3, or CN;
R5 is selected from the group consisting of H, CF3, CF2CF3, CN, and NO2; and
E is CH,
the method comprising:
converting
into
and
contacting
with
to provide the compound of formula (I),
wherein in the compound of formula (V):
R3 is selected from the group consisting of CF3, CF2CF3, CN, and NO2;
R4 is selected from the group consisting of CF3, CF2CF3, CN, and NO2; and
with the provisos that
if one of R3 and R4 is CN, then the other is CF2CF3 or NO2;
if one of R3 and R4 is NO2, then the other is CF3, CF2CF3, or CN.

### Claim 2 (depends on 1)

The method of claim 1, wherein converting (II) to (V) comprises:
a) brominating
to provide
b) deaminating
to provide
c) cyanating
to provide

### Claim 3 (depends on 2)

The method of claim 2, wherein brominating comprises contacting FeBr3 with the compound of formula (II).

### Claim 4 (depends on 3)

The method of claim 3, wherein the FeBr3 is generated in situ.

### Claim 5 (depends on 4)

The method of claim 4, wherein the compound of formula (II) contacts the FeBr3 after the FeBr3 is generated.

### Claim 6 (depends on 2)

The method of claim 2, wherein the deaminating of compound of formula (III) occurs via diazotization and warming.

### Claim 7 (depends on 2)

The method of claim 2, wherein monocyanation of the compound of formula (IV) comprises contacting the compound with a cyanide salt.

### Claim 8 (depends on 7)

The method of claim 7, wherein the cyanide salt is a transition metal cyanide salt.

### Claim 9 (depends on 8)

The method of claim 8, wherein the transition metal cyanide salt is CuCN.

### Claim 10 (depends on 1)

The method of claim 1, wherein the compound of formula (V) is contacted with the compound of formula (VI) in the presence of a Lewis acid.

### Claim 11 (depends on 10)

The method of claim 10, wherein the Lewis acid is Zn(OTf)2.

### Claim 12 (depends on 1)

The method of claim 1, wherein the compound of formula (V) is selected from the group consisting of: