An Experimentalists Guide to Electrosynthesis: The Shono Oxidation

Alfonso-Súarez, P, Kolliopoulos, AV, Smith, JP, Banks, CE ORCID: https://orcid.org/0000-0002-0756-9764 and Jones, AM ORCID: https://orcid.org/0000-0002-3897-5626 (2015) An Experimentalists Guide to Electrosynthesis: The Shono Oxidation. Tetrahedron Letters, 56 (49). pp. 6863-6867. ISSN 0040-4039

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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.

Item Type:	Article (Article)
Peer-reviewed:	Yes
Date Deposited:	15 Dec 2015 14:12
Publisher:	Elsevier
Additional Information:	NOTICE: this is the author’s version of a work that was accepted for publication in Tetrahedron Letters. Changes resulting from the publishing process, such as peer review, editing, corrections, structural formatting, and other quality control mechanisms may not be reflected in this document. Changes may have been made to this work since it was submitted for publication. A definitive version was subsequently published in Tetrahedron Letters, Vol 56, Issue 49, (2015) DOI 10.1016/j.tetlet.2015.10.090
Divisions:	Faculties > Science and Engineering
URI:	https://e-space.mmu.ac.uk/id/eprint/583974
DOI:	https://doi.org/10.1016/j.tetlet.2015.10.090
ISSN	0040-4039
e-ISSN	1873-3581

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