Cleavage of C-N bonds in guanidine derivatives and its relevance to efficient C-N bonds formation

Article abstract of DOI:10.1016/j.tet.2015.01.050

Efficient nonenzymatic decomposition of guanidine derivatives with high structural and functional diversity into anilide products is achieved in the presence of Pd^II/Cu(II) carboxylates/CO, relying on a dual C-N bonds cleavage strategy. In this decomposition process, the cooperative action of Pd^II species, Cu(II) carboxylates, and CO provides not only the N-acylating agents but also an initiator to trigger this C-N bonds cleavage sequence. The current results indicate that Pd^II/Cu(II) carboxylates/CO system provides a convenient and practical method for highly selective cleavage of unreactive C-N single bonds.