Novel and Direct Transformation of Methyl Ketones or Carbinols to Primary Amides by Employing Aqueous Ammonia

A novel and direct transformation of aryl, heteroaryl, vinyl, or ethynyl methyl ketones or carbinols to corresponding primary amides has been developed. An iodine-NH3·H2O system was proven to be efficient for this reaction and afforded the expected products with good yields in aqueous media. A tandem Lieben−Haller−Bauer reaction mechanism was involved in this type of reaction and is proposed for the first time.