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Representative Procedure for Formation of Amides from Alcohols via a Sequential Process. To an oven-dried, nitrogen-purged Schlenk tube charged with [Ir(Cp*)Cl2]2 (0.025 mmol) and cesium carbonate (16.4 mg, 0.05 mmol) were added alcohol (1 mmol, styrene (172 μL, 1.5 mmol, and degassed anhydrous toluene (2 cm3) via syringe, and the mixture was heated at reflux. The reaction was allowed to cool to room temperature and hydroxylamine hydrochloride (36.2 mg, 1 mmol) added. The vessel was flushed with nitrogen and the mixture further refluxed for 16 h. The reaction was allowed to cool to room temperature, diluted with dichloromethane, and filtered through a short plug of silica gel, and the solvent was removed in vacuo. The crude product was purified by column chromatography on silica gel or recrystallization from suitable solvent
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3) via syringe, and the mixture was heated at reflux. The reaction was allowed to cool to room temperature and hydroxylamine hydrochloride (36.2 mg, 1 mmol) added. The vessel was flushed with nitrogen and the mixture further refluxed for 16 h. The reaction was allowed to cool to room temperature, diluted with dichloromethane, and filtered through a short plug of silica gel, and the solvent was removed in vacuo. The crude product was purified by column chromatography on silica gel or recrystallization from suitable solvent
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