n‐Bu4NI/K2S2O8 Mediated Csp2−Csp2 Bond Cleavage – Transformylation from p‐Anisaldehyde to Primary Amides

Abstract

Abstractn‐Bu4NI/K2S2O8 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 Csp2−Csp2 bond cleavage.