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Azobisisobutyronitrile initiated aerobic oxidative transformation of amines: coupling of primary amines and cyanation of tertiary amines.

Organic letters (2012-10-31)
Lianghui Liu, Zikuan Wang, Xuefeng Fu, Chun-Hua Yan
ABSTRACT

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.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
2,2′-Azobis(2-methylpropionitrile), 98%
Sigma-Aldrich
2,2′-Azobis(2-methylpropionitrile) solution, 0.2 M in toluene
Sigma-Aldrich
Azobisisobutyronitrile, 12 wt. % in acetone
Sigma-Aldrich
2,2′-Azobis(2-methylpropionitrile), recrystallized from methanol, 99%

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