Copper(i) Iodide-Catalyzed Synthesis of N,N′-Disubstituted Guanidines from N-Substituted Cyanamides*

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A facile and effective synthesis of N-alkyl-N′-arylguanidines was accomplished by the reaction of N-arylcyanamides with various primary and secondary alkylamines, under the catalysis of copper(i) iodide and Xantphos in DMF. This methodology provides a direct access to versatile N,N′-disubstituted guanidine derivatives from N-arylcyanamides that can be readily prepared from the corresponding nitriles via Tiemann rearrangement.