Recent Developments in Shono-Type Oxidation: Strategies for Modular α-C(sp 3 )–H Functionalization
Year: 2025
Type: article
Abstract: High Resolution Image Download MS PowerPoint Slide The Shono oxidation has served as a pillar in synthetic organic electrochemistry for over 50 years, demonstrating streamlined α-C(sp 3 )–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(sp 3 )–H functionalization beyond canonical C–O bond formation, focusing on improved two-step protocols, redox mediator approaches, and selective iminium ion formation.
Source: ACS electrochemistry.
Authors: Siyuan Su, Yahui Guo, Joseph Derosa
Institution: Boston University
Language: English
Subfield: Organic Chemistry
Field: Chemistry
Domain: Physical Sciences
Open Access status: bronze
Funder: Boston University
OpenAlex ID: W4417516319