An
operationally simple oxidation–cyanation method for the
synthesis of cyanamides is described. The procedure utilizes inexpensive
and commercially available N-chlorosuccinimide and
Zn(CN)2 as reagents to avoid direct handling of toxic cyanogen
halides. It is demonstrated to be amenable for the cyanation of a
variety of primary and secondary amines and aniline derivatives as
well as a complex synthetic intermediate en route to verubecestat
(MK-8931). Additionally, kinetic measurements and other control experiments
are reported to shed light onto the mechanism of this cyanation reaction.
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