Categories: C-N Bond Formation >
Synthesis of Cyanamides
An operationally simple oxidation-cyanation enables the synthesis of cyanamides using inexpensive and commercially available N-chlorosuccinimide and Zn(CN)2 as reagents. The method avoids the direct handling of toxic cyanogen halides and is amenable for the cyanation of various primary and secondary amines and aniline derivatives.
N. Kuhl, S. Raval, R. D. Cohen, Org. Lett., 2019, 21, 1268-1272.
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.
C. Zhu, J.-B. Xia, C. Chen, Org. Lett., 2014, 16, 247-249.
Cyanamides were selectively formed in good yields through a one-step nucleophilic substitution reaction of allylic tertiary amines with cyanogen bromide under mild reaction conditions via N-deallylation and N-cyanation in one pot.
H. Liang, L. Bao, Y. Du, Y. Zhang, S. Pang, C. Sun, Synlett, 2017, 28, 2675-2679.