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In the presence of a catalytic amount of radical initiator AIBN, 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.


Lianghui Liu, Zikuan Wang, Xuefeng Fu, Chun-Hua Yan. Azobisisobutyronitrile initiated aerobic oxidative transformation of amines: coupling of primary amines and cyanation of tertiary amines. Organic letters. 2012 Nov 16;14(22):5692-5

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PMID: 23106189

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