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.

DOI: 10.1021/acs.joc.8b02190

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Abstract

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.

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Proposed Mechanism for the Dehydration of Amides under Catalytic Swern Conditions

Proposed Mechanism for the Dehydration of Aldoximes under Catalytic Swern Conditions

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Key Words

nitriles, Swern oxidation, oxalyl chloride

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ID: J42-Y2018