A simple and efficient radical coupling of 2-isocyanobiphenyl with ethers was developed, providing a variety of 6-alkylated phenanthridines. Both cyclic and acyclic ethers are suitable substrates for this transformation, which comprised the functional- ization of two C-H bonds: the sp3 C-H of ether and sp2 C-H of phenyl group. The kinetic isotope effect (KIE) revealed that the cleavage of sp3 C-H bond would be involved in the rate-determining step.
A new copper and silver-mediated cyanation of aryl iodides with DDQ as a cyanide source is achieved, provid- ing nitriles with good yields. This new approach represents a safe method leading to aryl nitriles.