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. 2014 Jan 3;16(1):247-9.
doi: 10.1021/ol403245r. Epub 2013 Dec 6.

A simple method for the electrophilic cyanation of secondary amines

Chen Zhu  1 , Ji-Bao Xia, Chuo Chen
Affiliations

A simple method for the electrophilic cyanation of secondary amines

Chen Zhu et al. Org Lett. .

Abstract

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

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Figures

Figure 1
Figure 1
Scope of the N-cyanation reaction. aReaction conditions: 3.0 equiv NaClO (aq), 2.0 equiv TMSCN, 24 h.
Figure 2
Figure 2
Crystal structure of 5.
Figure 3
Figure 3
13C NMR spectrum of the reaction of TMSCN and NaClO in CDCl3 after 5 min.
Figure 4
Figure 4
Proposed mechanism for the N-cyanation reaction.
See this image and copyright information in PMC

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