Stereochemistry of the remote oxidative cyanation of methylcyclohexanones

Electrochemical synthesis of CN-substituted imidazo[1,5-a]pyridines via a cascade process using NH4SCN as both an electrolyte and a non-trivial cyanating agent

“…The cyano group is one of the versatile synthons in organic chemistry, and much effort has been directed towards developing cyanation methods. [1][2][3][4][5][6][7][8][9] Recently, in view of the toxicity of metal cyanides, "non-metal" organic [CN] sources such as acetonitrile, tosyl cyanide (TsCN), 2,2′-azobis-(isobutyronitrile) (AIBN), 10,11 N-cyanosuccinimide, and N-cyano-N-phenyl-ptoluenesulfonamide (NCTS) 12 as well as combined [CN] sources ([NH 3 ] with DMF or DMSO) have become attractive (Scheme 1). [13][14][15][16][17] Thiocyanate salt oxidation has been shown to produce cyanide ions under the action of various chemical oxidants.…”