Synthesis of Nitriles from Primary Amides or Aldoximes under Conditions of a Catalytic Swern Oxidation
Rui Ding, Yongguo Liu, Mengru Han, Wenyi Jiao, Jiaqi Li, Hongyu Tian*, Baoguo Sun*
*Beijing Advanced Innovation Center for Food Nutrition and Human Health, Beijing Key Laboratory of Flavor Chemistry, Beijing Technology and Business University, Beijing 100048, China, Email: tianhybtbu.edu.cn, sunbgbtbu.edu.cn
R. Ding, Y. Liu, M. Han, W. Jiao, J. Li, H. Tian, B. Sun, J. Org. Chem., 2018, 83, 12939-12944.
see article for more reactions
The use of oxalyl chloride with a catalytic amount of dimethyl sulfoxide in the presence of Et3N enables the preparation of nitriles from primary amides or aldoximes within 1 h at room temperature. A diverse range of nitriles were obtained in good to excellent yields, including aromatic, heteroaromatic, cyclic, and acyclic aliphatic compounds.
see article for more examples
Proposed Mechanism for the Dehydration of Amides under Catalytic Swern Conditions
Proposed Mechanism for the Dehydration of Aldoximes under Catalytic Swern Conditions