2‐Cyanopyridazin‐3(2H)‐ones: Effective and Chemoselective Electrophilic Cyanating Agents.

Abstract

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Recent Advances in Cyanamide Chemistry: Synthesis and Applications

“…The electrophilic cyanation of secondary amines is the most prevalent method used to access disubstituted cyanamides, with cyanogen bromide (BrCN) being the most common reagent. Though cheap and effective, the toxicity associated with this reagent has prompted the development of safer cyanating agents such as 2-cyanopyridazin-3(2 H )-one, cyanobenzimidazole, and 1-cyanoimidazole [ 4 , 5 , 6 ].…”

“…While NCTS is the reagent of choice for many transition metal catalyzed cyanation protocols, efforts have also been directed towards the development of transition-metal-free conditions. An early example of NCTS for cyanation under metal-free conditions was reported by the groups of Beller and Wang [ 4 , 63 ]. Beller and colleagues employed NCTS in the direct cyanation of aryl and heteroaryl-halides via in situ generated Grignard reagents, to synthesize a diverse array of benzonitrile derivatives.…”