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US 7,442,800 B2Granted
Nucleophilic heterocyclic carbene derivatives of Pd(acac)2 for cross-coupling reactions
AssigneePromerus, LLC
InventorsDino Amoroso, Andrew Bell, Oscar Navarro Fernandez, Steven P. Nolan, Nicolas Marion
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Abstract
Embodiments in accordance with the present invention provide for a palladium complex characterized by the general formula: where A is a bidentate monoanionic ligand, NHC is a nucleophilic heterocyclic carbene, and Z is an anionic ligand. Such palladium complexes are useful in initiating cross-coupling reactions.
Claims39
A palladium complex characterized by the general formula:
- where A is a bidentate monoanionic ligand, NHC is a nucleophilic heterocyclic carbene, and Z is an anionic ligand.
A process of forming a carbon-carbon or a carbon-heteroatom bond comprising:
- providing a palladium complex represented by Formula I:
- where NHC is a nucleophilic heterocyclic carbene;
- Z is an anionic ligand;
- and A is a bidentate monoanionic ligand represented by Formula II:
- and further where each of X and Y is independently one of O, N, or S and where R1, R2, R3, R4, R5, R6 and R7 each independently represent hydrogen, methyl, linear or branched C2-C10 alkyl, C3-C10 cycloalkyl, C7-C20 aralkyl, or C6-C24 aryl or substituted aryl, subject to the proviso that R1and R5 are only present when X and/or Y is N;
- n represents an integer of 0, 1, or 2;
- and Z is one of Cl, Br, I, OAc, OMs, OTf, OTs, O2CCF3, acetylacetonate (acac), trifluoroacetylacetonate, hexafluoroacetylacetonate (hfacac);
- dibenzoylmethanate (dbm), benzoylacetonate (bac), or tetramethylheptanedionate (tmhd);
- and
- forming a carbon-carbon or carbon-heteroatom bond using one of the Suzuki, Suzuki-Miyaura, Murahashi, Kumada, Kumada-Corriu, Kumada-Tamao, Nozaki, Nozaki-Oshima, Negishi, Hiyama, Tamao-Kumada, Hiyama-Hatanaka, Stille, Migita-Kosugi, Buchwald-Hartwig, Murahashi, Cyanation, dehydrohalogenation, α-“Carbonyl” Arylation, Sonogashira , Cadiot-Chodkiewicz, Heck reactions, catalytic ether formation, catalytic α-arylations of ketones, dehalogenation, and catalytic thioether formation reactions, substrates and reactive partners thereof.
7 more elements
Dependencies are inferred from the claim text.