N-heterocyclic carbene (NHC) based ligands and related methods

Patent metadata

Field	Value
Publication number	US-10843178-B2
Application number	US-201816105532-A
Country	US
Kind code	B2
Filing date	Aug 20, 2018
Priority date	Aug 18, 2017
Publication date	Nov 24, 2020
Grant date	Nov 24, 2020

Abstract

Polydentate macrocyclic NHCs (NHC ligands) and related methods are disclosed. Such ligands advantageously facilitate a variety of ligand coordination modes and stabilize oxidation states of metal complexes with a number of coordination environments and shapes. The NHC ligands described herein comprise pendant groups configured to facilitate a variety of reactions including: cis-trans isomerization, proton shuttling and facilitating changes in coordination environments as a result of redox reactions.

First claim

The invention claimed is:

1. AN-heterocyclic carbene (NHC) ligand comprising cis- or trans-isomers of the compound of formula (1) or a salt thereof:

wherein:
R 1 and R 2 are each, individually, hydrogen, a substituted or unsubstituted C1 to C10 hydrocarbyl group, or R 1 and R 2 together form a saturated or unsaturated C3 to C10 ring;
R 3 and R 4 are each, individually, hydrogen, a substituted or unsubstituted C1 to C10 hydrocarbyl group, or R 3 and R 4 together form a saturated or unsaturated C3 to C10 ring;
R 5 and R 6 are substituted or unsubstituted C1 to C10 hydrocarbyl groups; and
x is an integer from 1 to 6, and wherein cis or trans refers to the relationship of NR 5 and NR 6 .

2. The ligand of claim 1 , wherein R 1 , R 2 , R 3 , and R 4 are each hydrogen, forming a compound of Formula (II):

3. The ligand of claim 1 , wherein R 5 and R 6 are both benzyl CH 2 C 6 H 5 groups.

4. The ligand of claim 1 , wherein the composition comprises a salt and the salt is a halide salt.

5. The ligand of claim 1 , wherein the composition comprises a trans isomer.

6. The ligand of claim 1 , wherein R 1 , R 2 , R 3 , and R 4 are each hydrogen, and R 5 and R 6 are each benzyl CH 2 C 6 H 5 group, and the ligand is the trans-isomer.

Assignees

• Univ Arkansas

Inventors

• Kilyanek Stefan M
• Thapa Rajesh

Classifications

• C07D403/12 Primary

  linked by a chain containing hetero atoms as chain links · CPC title

• B01J2540/40

  Non-coordinating groups comprising nitrogen · CPC title

• B01J2231/4261

  Heck-type, i.e. RY + C=C, in which R is aryl · CPC title

• B01J2231/4211

  Suzuki-type, i.e. RY + R'B(OR)2, in which R, R' are optionally substituted alkyl, alkenyl, aryl, acyl and Y is the leaving group · CPC title

• B01J2531/17

  Silver · CPC title