An experimentalist's guide to electrosynthesis: the Shono oxidation. Issue 49 (9th December 2015)

• Record Type: Journal Article
• Authors: Alfonso-Súarez, Paulino; Kolliopoulos, Athanasios V.; Smith, Jamie P.; Banks, Craig E.; Jones, Alan M.
• Is Part Of: Tetrahedron letters. Volume 56:Issue 49(2015)
• Page Start: 6863
• Page End: 6867
• Publication Date: 2015-12-09
• Subjects: Electrochemistry -- Electrosynthesis -- Shono oxidation -- Anodic methoxylation -- Potentiometry -- Cyclic voltammetry; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2015.10.090
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Abstract: Electrosynthesis is a powerful method to functionalise organic molecules without the need to use chemical reagents or protecting groups, yet it is not widely used in synthesis. In this study, we investigated the Shono oxidation of a tertiary amide (electrochemical functionalisation of a C–H bond adjacent to an amide nitrogen atom), demonstrating the value of performing cyclic voltammetry, varying voltage and charge per mole, selection of electrolyte and electrode material. We demystify the process to demonstrate a simple relationship between oxidation potential, and charge transfer required, which affords a high conversion to the desired alpha-methoxylated product using an undivided experimental cell.