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

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

441090

Sigma-Aldrich

2,2′-Azobis(2-methylpropionitrile), 98%

11630

Sigma-Aldrich

2,2′-Azobis(2-methylpropionitrile), purum, ≥98.0% (GC)

714887

Sigma-Aldrich

2,2′-Azobis(2-methylpropionitrile) solution, 0.2 M in toluene

755745

Sigma-Aldrich

2,2′-Azobis(2-methylpropionitrile), recrystallized from methanol, 99%

768375

Sigma-Aldrich

Azobisisobutyronitrile, 12 wt. % in acetone