Organic Chemistry Portal



Reductive Deuteration of Nitriles: The Synthesis of α,α-Dideuterio Amines by Sodium-Mediated Electron Transfer Reactions

Yuxuan Ding, Shihui Luo, Adila Adijiang, Hongye Zhao, Jie An*

*College of Science, China Agricultural University, No. 2 Yuanmingyuan West Road, Beijing 100193, China, Email:

Y. Ding, S. Luo, A. Adijiang, H. Zhao, J. An, J. Org. Chem., 2018, 83, 12269-12274.

DOI: 10.1021/acs.joc.8b01730


A practical and cost-efficient reductive deuteration of nitriles under single-electron transfer conditions enables the synthesis of α,α-dideuterio amines in excellent yields using bench stable and commercially available sodium dispersions and EtOD-d1.

see article for more examples

Reductive Cleavage of Unactivated Carbon-Cyano Bonds under Ammonia-Free Birch Conditions

Y. Ding, S. Luo, L. Ma, J. An, J. Org. Chem., 2019, 84, 15827-15833.

Key Words

reduction of nitriles, sodium

ID: J42-Y2018