<i>N</i>‑Cyanation of Secondary Amines Using Trichloroacetonitrile

A one-pot <i>N</i>-cyanation of secondary amines has been developed using trichloroacetonitrile as an inexpensive cyano source. A diverse range of cyclic and acyclic secondary amines can be readily transformed into the corresponding cyanamides in good isolated yields, with the method successfully utilized in the final synthetic step of a biologically active rolipram-derived cyanamide. This approach exhibits distinct selectivity when compared to the use of highly toxic cyanogen bromide

Deoxycyanamidation of Alcohols with <i>N</i>‑Cyano‑<i>N</i>‑phenyl-<i>p</i>-methylbenzenesulfonamide (NCTS)

The first one-pot deoxycyanamidation of alcohols has been developed using <i>N</i>-cyano-<i>N</i>-phenyl-<i>p</i>-methyl­benzene­sulfonamide (NCTS) as both a sulfonyl transfer reagent and a cyanamide source, accessing a diverse range of tertiary cyanamides in excellent isolated yields. This approach exploits the underdeveloped desulfonylative (N–S bond cleavage) reactivity pathway of NCTS, which is more commonly employed for electrophilic <i>C</i>- and <i>N</i>-cyanation processes