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Azobisisobutyronitrile Initiated Aerobic Oxidative Transformation of Amines: Coupling of Primary Amines and Cyanation of Tertiary Amines

Lianghui Liu, Zikuan Wang, Xuefeng Fu* and Chun-Hua Yan

*Beijing National Laboratory for Molecular Sciences, State Key Lab of Rare Earth Materials Chemistry and Applications, College of Chemistry and Molecular Engineering, Peking University, Beijing, 100871, P. R. China, Email: fuxfpku.edu.cn

L. Liu, Z. Wang, X. Fu, C.-H. Yan, Org. Lett., 2012, 14, 5692-5695.

DOI: 10.1021/ol302708r (free Supporting Information)



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Abstract

In the presence of oxygen and a small amount of AIBN as radical initiator, primary amines are oxidatively coupled to imines and tertiary amines are cyanated to α-aminonitriles. These metal-free aerobic oxidative coupling reactions may find applications in a wide range of green oxidation chemistry.

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Key Words

cyanation, α-amino acid derivatives, oxygen, green chemistry


ID: J54-Y2012-3650