Angewandte Chemie International Edition · 2014 · 185 citations · 81 references
Natural SciencesChemistryMedicinal ChemistryOrganic ChemistryOrganic SynthesisAmide Bond FormationArylation ReactionsChemoselective FunctionalizationChemoselective SynthesisElectrophilic CatalysisEster-to-amide ConversionKetones
A new approach for the fully chemoselective α-arylation of amides is presented. By means of electrophilic amide activation, aryl groups can be regioselectively introduced α- to amides, even in the presence of esters and alkyl ketones. Mechanistic studies reveal key reaction intermediates and emphasize a remarkably subtle base effect in this transformation.
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