Recent Developments in Shono-Type Oxidation: Strategies for Modular α-C(sp ³ )–H Functionalization

The Shono oxidation has served as a pillar in synthetic organic electrochemistry for over 50 years, demonstrating streamlined α-C(sp3)–H functionalization of saturated azacycles via N,O-acetal intermediates that can be derivatized in subsequent chemical steps. These direct anodic oxidations, however, historically present challenges related to functional group tolerance and site-selectivity and can result in deleterious side reactivity. These obstacles have hampered general applications in complex molecule synthesis and late-stage functionalization, motivating new approaches to realize selective Shono-type functionalization reactions. Over the past decade, a variety of strategies building on this traditional platform have sought to expand reaction scope and selectivity. This Perspective highlights recent developments toward harnessing Shono oxidation for programmable α-C(sp3)–H functionalization beyond canonical C–O bond formation, focusing on improved two-step protocols, redox mediator approaches, and selective iminium ion formation.