n-Bu(4)NI/K(2)S(2)O(8) Mediated Csp(2)-Csp(2) Bond Cleavage - Transformylation from p-Anisaldehyde to Primary Amides

n-Bu(4)NI/K(2)S(2)O(8) mediated transformylation from p-anisaldehyde to primary amides is reported. The mechanistic studies suggest the reaction occurs via a single electron transfer pathway. Based on the DFT electronic structure calculations of various reaction pathways, the most plausible mechanism involves the formation of a phenyl radical cation and an arenium ion as the key intermediates. It represents the first example where p-anisaldehyde is employed as a formyl source via a non-metal mediated Csp(2)-Csp(2) bond cleavage.