Journal of the American Chemical Society · 2012 · 449 citations · 53 references
Natural SciencesChemistryCatalysisInorganic ChemistryOrganic ChemistryAddition ReactionsChemical BondingCoordination ChemistryOrganic SynthesisAmino FunctionalizationArene CoordinationArene FunctionalizationFunctional Group ToleranceOxidant Chemistry
We report the direct amidation of arene C-H bonds using sulfonyl azides as the amino source to release N(2) as the single byproduct. The reaction is catalyzed by a cationic rhodium complex under external oxidant-free conditions in the atmospheric environment. A broad range of chelate group-containing arenes are selectively amidated with excellent functional group tolerance, thus opening a new avenue to practical intermolecular C-N bond formation.
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Frédéric Paul, Joe Patt, John F. Hartwig · Journal of the American Chemical Society · 1994 · 835 citations