N-heterocyclic carbene-amido palladium(II) catalysts and method of use thereof
AssigneeUniversity of Southern California
InventorsKyung Woon Jung, Kyung Soo Yoo, Satoshi Sakaguchi, Chan Phil Park, Justin O'Neill, Joo Ho Lee
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Abstract
A new N-heterocyclic catalyst system which contains N-heterocyclic carbene and amido as ligands, which are strongly bound to a palladium metal. Another heteroatom functionality can be used as a third ligand L. The NHC-amidate ligand system is unique in structure, and shows excellent reactivities in a number of chemical reactions. The chemical reactions include carbon-carbon and carbon-heteroatom (oxygen and nitrogen) bond formations, and oxidation reactions of saturated carbon chemicals via C—H activation.
Claims18
An N-Heterocyclic carbene-amido palladium(II) catalyst having a chemical structure according to general formula I:
- wherein R1 and R5 may be the same or different and are selected from the group consisting of H, alkyl of 1 to 10 carbon atoms, aryl of 1 to 10 carbon atoms, and aralkyl of 1 to 10 carbon atoms, and may optionally contain one or more heteroatoms;
- R2 is selected from the group consisting of H, alkyl of 1 to 10 carbon atoms, aryl of 1 to 10 carbon atoms, and aralkyl of 1 to 10 carbon atoms, or optionally forms part of a linkage to form a dimer;
- R3 and R4 is selected from the group consisting of H and an aryl ring of from 4 to 8 carbon atoms;
- R6 is selected from the group consisting of H and alkoxy having 1-4 carbon atoms;
- and L is selected from the group consisting of a halogen or optionally forms part of a linkage to form a dimer,
- wherein the linkage from R1 to the ring carbon is either chiral or achiral, and
- wherein the chemical structure may be in a dimeric form.
A method of forming a bond between a carbon atom and a second atom, wherein the method involves the step of contacting a first reactant containing the carbon atom and a second reactant containing the second atom in the presence of an N-Heterocyclic carbene-amido palladium(II) catalyst having a general formula (I):
- where R1 and R5 may be the same or different and are selected from the group consisting of H, alkyl of 1 to 10 carbon atoms, aryl of 1 to 10 carbon atoms, and aralkyl of 1 to 10 carbon atoms, and may optionally contain one or more heteroatoms;
- R2 is selected from the group consisting of H, alkyl of 1 to 10 carbon atoms, aryl of 1 to 10 carbon atoms, and aralkyl of 1 to 10 carbon atoms, or optionally forms part of a linkage to form a dimer;
- R3 and R4 is selected from the group consisting of H and aryl ring of from 4 to 8 carbon atoms;
- R6 is selected from the group consisting of H and alkoxy of 1-4 carbon atoms;
- and L is selected from the group consisting of a halogen or optionally forms part of a linkage to form a dimer,
- wherein the linkage from R1 to the ring carbon is either chiral or achiral, and
- wherein the chemical structure may be in a dimeric form.
Dependencies are inferred from the claim text.