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A Simple Method for the Electrophilic Cyanation of Secondary Amines

Chen Zhu, Ji-Bao Xia and Chuo Chen*

*University of Texas Southwestern Medical Center, Department of Biochemistry, 5323 Harry Hines Boulevard, Dallas, Texas 75390, United States, Email:

C. Zhu, J.-B. Xia, C. Chen, Org. Lett., 2014, 16, 247-249.

DOI: 10.1021/ol403245r (free Supporting Information)


Bleach oxidizes trimethylsilyl cyanide to generate an electrophilic cyanating reagent that readily reacts with an amine nucleophile. This oxidative N-cyanation reaction enables the synthesis of disubstituted cyanamides without using highly toxic cyanogen halides.

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Key Words

cyanamides, bleach

ID: J54-Y2014