Transition metal complexes for enantioselective catalysis of carbon-carbon, carbon-heteroatom, and carbon-hydrogen bond forming reactions

Patent metadata

Field	Value
Publication number	US-10189871-B2
Application number	US-201615243054-A
Country	US
Kind code	B2
Filing date	Aug 22, 2016
Priority date	Jul 27, 2012
Publication date	Jan 29, 2019
Grant date	Jan 29, 2019

Abstract

In some embodiments, the present disclosure pertains to a compound, comprising a transition metal complex having the formula Φ-[M (x,y)-L1 (w,v)-L2 (t,u)-L3]p+An−mZ−p−m. In an embodiment of the present disclosure Φ may be Λ. In another embodiment Φ may be Δ. In some embodiments of the present disclosure, M is a transition metal. In a related embodiment, p is an integer corresponding to the oxidation state of M. In some embodiments of the present disclosure, each of x, y, w, v, t, and u independently comprise R. In other embodiments, each of x, y, w, v, t, and u independently comprise S. In an embodiment of the present disclosure, each of L1, L2, and L3 independently is a ligand comprising a substituted diamine. In some embodiments, An− comprises a lipophilic anion, where m is from 1 to 3, and where Z− comprises an optional second anion.

First claim

What is claimed is:

1. A compound, comprising a transition metal complex having the formula Φ-[M ((x,y)-L 1 ) 3−b−c ((w,v)-L 2 ) b ((t,u)-L 3 ) c ] p+ An − m ,Z − p−m , wherein Φ is Λ or Δ, wherein M is a transition metal, wherein p is an integer corresponding to the oxidation state of M, wherein each of x, y, w, v, t, and u independently comprises one of R and S, wherein each of L 1 and L 2 independently is a ligand comprising ethylene diamine, wherein L 3 is EN(CH 2 ) n NR 1 R 2 , wherein EN represents ethylene diamine, wherein n is from 2 to 4, and wherein R 1 and R 2 are independently H or alkyl groups, wherein c is from 1 to 3, wherein b is from 0 to 2, wherein An − comprises a lipophilic anion, wherein m is from 1 to 3, and wherein Z − comprises a second anion.

2. The transition metal complex according to claim 1 , wherein the transition metal is selected from the group consisting of cobalt, iron, nickel, chromium, manganese, molybdenum, tungstsen, rhenium, ruthenium, technetium, osmium, rhodium, iridium, platinum, and palladium.

3. The transition metal complex according to claim 1 , wherein the lipophilic anion is selected from the group consisting of tetrakis[(3,5-trifluromethyl)phenyl]borate), tetrakis[pentafluorophenyl]borate, carboranes of the general formula CB 11 H 12 − , TRISPHAT of the general formula P(O 2 C 6 Cl 4 ) 3− , and 1,1′-Binaphthyl-2,2′-diyl phosphates.

4. The transition metal complex according to claim 1 , wherein the transition metal complex has an enantioselectivity of at least 60% for one or more of a carbon-carbon bond forming reaction, a carbon-heteroatom bond forming reaction, and a carbon-hydrogen bond forming reaction.

5. The transition metal complex catalyst according to claim 1 , wherein the transition metal complex has a conversion rate of at least 95% for the one or more of a carbon-carbon bond forming reaction, a carbon-heteroatom bond forming reaction, and a carbon-hydrogen bond forming reaction.

Assignees

• Lewis Kyle G
• Gladysz John A
• Ghosh Subrata K
• Texas A & M Univ Sys

Inventors

• Lewis Kyle G
• Gladysz John A
• Ghosh Subrata K

Classifications

• C07F15/065 Primary

  without a metal-carbon linkage · CPC title

• C07F5/027

  Organoboranes and organoborohydrides · CPC title

• B01J31/2295

  Cyclic compounds, e.g. cyclopentadienyls · CPC title

• B01J2231/32

  Addition reactions to C=C or C-C triple bonds · CPC title

• B01J31/22

  Organic complexes · CPC title