Categories: C-N Bond Formation >
Synthesis of Cyanamides
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Recent Literature
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.