Biaryl ligands

Patent metadata

Field	Value
Publication number	US-9994599-B2
Application number	US-201415021053-A
Country	US
Kind code	B2
Filing date	Sep 12, 2014
Priority date	Sep 13, 2013
Publication date	Jun 12, 2018
Grant date	Jun 12, 2018

Abstract

Embodiments of the present disclosure provide for biaryl ligands (also referred to herein as “biaryl compound”), biaryl complexes, methods of making biaryl compounds, methods of making single enantiomers of these biaryl compounds, methods of use (e.g., catalysis) and the like.

First claim

At least the following is claimed:

1. A The composition comprising a single biaryl enantiomer having the following structure:

wherein each of the R 5 groups is independently selected from the group consisting of: hydrogen, a halogen group, a cyclic or linear, alkyl group, an aryl group, a —OR group, and a —SR group, wherein each of R group is independently selected from the group consisting of: hydrogen, a cyclic or linear alkyl group, and an aryl group, wherein n is 1 to 5,
wherein X is C or SO 2 , wherein each R 6 and R 7 group is independently selected from the group consisting of: hydrogen, a cyclic or linear alkyl group, and an aryl group, wherein when X is SO 2 , R 6 and R 7 are not present;
wherein each of Q1, Q2, Q3, Q4, and Q5 is independently selected from the group consisting of C, N, O, and S, wherein at least one of Q1, Q2, Q3, Q4, and Q5 is selected from the group consisting of N, O, and S, wherein R 1 and R 2 are independently selected from the group consisting of: hydrogen, a halogen group, a cyclic or linear, alkyl group, an aryl group, a —OR group, and a —SR group; and
wherein each of the R 4 groups is independently selected from the group consisting of: hydrogen, a halogen group, a cyclic or linear, alkyl group, an aryl group, a —OR group, and a —SR group, wherein m is 1 to 5,
wherein each of the R 3 groups is independently selected from the group consisting of: hydrogen, a cyclic or linear, alkyl group, an alkoxide, a phenoxide, an aryl group, and a substituted amine.

2. The composition of claim 1 , wherein each R 5 is halogen, wherein two of Q1, Q2, Q3, Q4, and Q5 are N, wherein X is C, and wherein each R 3 is an aryl group.

3. The composition of claim 2 , wherein Q2 and Q5 are N.

4. The composition of claim 2 , wherein each R 3 is a phenyl group.

5. The composition of claim 2 , wherein each R 5 is fluorine.

6. A composition comprising: a single biaryl enantiomer having the following structure:

wherein each of the R 5 groups is independently selected from the group consisting of: hydrogen, a halogen group, a cyclic or linear, alkyl group, an aryl group, a —OR group, and a —SR group, wherein each of R group is independently selected from the group consisting of: hydrogen, a cyclic or linear alkyl group, and an aryl group, wherein n is 1 to 5,
wherein X is C or SO 2 , wherein each R 6 and R 7 group is independently selected from the group consisting of: hydrogen, a cyclic or linear, alkyl group, and an aryl group, wherein when X is SO 2 , R 6 and R 7 are not present,
wherein R 1 and R 2 are independently selected from the group consisting of: hydrogen, a halogen group, a cyclic or linear, alkyl group, an aryl group, a —OR group, and a —SR group,
wherein each of the R 4 groups is independently selected from the group consisting of: hydrogen, a halogen group, a cyclic or linear, alkyl group, an aryl group, a —OR group, and a —SR group, wherein m is 1 to 5, and
wherein each of the R 3 groups is independently selected from the group consisting of: hydrogen, a cyclic or linear, alkyl group, an alkoxide, a phenoxide, an aryl group, and a substituted amine.

7. The composition of claim 6 , wherein X is C, wherein each R 3 is a phenyl group, and wherein each R 5 is fluorine.

8. A composition comprising: a structure selected from the group consisting of:

Assignees

• Univ Florida

Inventors

• Aponick Aaron
• Cardoso Flavio S P

Classifications

• C07D233/20 Primary

  with substituted hydrocarbon radicals, directly attached to ring carbon atoms · CPC title

• C07F9/6506 Primary

  having the nitrogen atoms in positions 1 and 3 · CPC title

• C07D211/74

  Oxygen atoms · CPC title

• C07C209/22

  by substitution of other functional groups · CPC title

• C07F7/083

  Syntheses without formation of a Si-C bond · CPC title