Biaryl ligands, methods of making biaryl ligands, and methods of use thereof

Patent metadata

Field	Value
Publication number	US-10618922-B2
Application number	US-201815927505-A
Country	US
Kind code	B2
Filing date	Mar 21, 2018
Priority date	Sep 13, 2013
Publication date	Apr 14, 2020
Grant date	Apr 14, 2020

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 composition comprising a single biaryl compound having the following structure:

wherein MET is selected from a transition metal, wherein z is 1 to 3, wherein L is a ligand, wherein u is 0 or 1 to 5;
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; 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.

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 1 , wherein each R 5 is fluorine.

6. The composition of claim 1 , wherein the transition metal is selected from the group consisting of: Fe, Co, Ni, Ru, Rh, Pd, Os, Ir, Pt, Cu, and Au.

7. The composition of claim 1 , wherein the ligand is selected from the group consisting of: amide, phenolate, thiolate, halogen, carboxylate, acetylacetonate, phosphine, phosphite, and phosphoramidite.

8. A composition comprising: a single biaryl compound having the following structure:

wherein MET is selected from a transition metal, wherein z is 1 to 3, wherein L is a ligand, wherein u is 0 or 1 to 5;
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, 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.

9. The composition of claim 8 , wherein X is C, wherein each R 3 is a phenyl group, and wherein each R 5 is fluorine.

10. The composition of claim 8 , wherein the transition metal is selected from the group consisting of: Fe, Co, Ni, Ru, Rh, Pd, Os, Ir, Pt, Cu, and Au.

11. The composition of claim 8 , wherein the ligand is selected from the group consisting of: amide, phenolate, thiolate, halogen, carboxylate, acetylacetonate, phosphine, phosphite, and phosphoramidite.

Assignees

• Univ Florida

Inventors

• Aponick Aaron
• Cardoso Flavio S P

Classifications

• B01J2231/766

  of -CH-CH- or -C=C- to -C=C- or -C-C- triple bond species · CPC title

• C07D211/74

  Oxygen atoms · CPC title

• C07F9/6506 Primary

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

• C07F7/083

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

• C07D233/20 Primary

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