Advanced Synthesis & Catalysis · 2010 · 51 citations · 50 references
Natural SciencesChemistryInorganic ChemistryOrganic ChemistryOrganometallic ChemistryChemical ReactionsCoordination ChemistryHeterocyclic ChemistryReductive Cross-coupling
Abstract The reductive formation of substituted anilines from amines and three well‐defined aryl‐ gold(III) complexes, i.e., dichloro(2,6‐lutidine)phen‐ ylgold(III) ( 2 ), dichloro(2,6‐lutidine)‐ p ‐tolylgold(III) ( 3 ), and chlorobis(triphenylphosphine)phenylgold(III) chloride ( 4 ) was studied. The reaction is stoichiometric in gold and represents a key step of a potential gold‐catalyzed intermolecular amination reaction of arenes. It proceeds smoothly with a broad range of N ‐nucleophiles in the presence of sodium acetate (NaOAc) and enables the selective formation of N ‐substituted anilines in good yields. A mechanistic pathway is proposed and discussed as well.
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Frédéric Paul, Joe Patt, John F. Hartwig · Journal of the American Chemical Society · 1994 · 835 citations