Synthesis of β-Amino-α-iminonitriles and α,β-Diiminonitriles Enabled by Lewis Acid-Catalyzed Double Isocyanide Insertion with Imines

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Lewis acid-catalyzed double isocyanide insertion with imines was disclosed for the efficient construction of synthetically useful functionalized iminonitriles in a chemoselective manner. Zn(OTf) 2 catalyzed the synthesis of β-amino-α-iminonitriles from ketimines, while in the case of aldimines, α,β -diiminonitriles could be achieved either from the oxidation of the obtained β-amino-α-iminonitriles or through the In(OTf) 3 -catalyzed one-pot oxidative isocyanide insertion. Furthermore, various transformations of the versatile product demonstrate the remarkable synthetic potential inherent in the given protocol.