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Organic electrosynthesis using a fluoride ion mediator

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Abstract Recent studies on fluoride ion-mediated anodic methoxylation of fluoroalkyl sulfides and sulfur-containing five-membered heterocyclic compounds together with its synthetic applications are summarized in this review. The first example of… Click to show full abstract

Abstract Recent studies on fluoride ion-mediated anodic methoxylation of fluoroalkyl sulfides and sulfur-containing five-membered heterocyclic compounds together with its synthetic applications are summarized in this review. The first example of anodic methoxylation of 2-acyloxy-3,3,3-trifluoropropyl sulfides accompanying with [1,2]-rearrangement of acyloxy group is described. Fluoride ion-mediated anodic intramolecular cyclization of 3,3,3-trifluoropropyl sulfides bearing OH and t-BuCOO groups provides CF3-containing 1,3-oxathiolane and ethylene carbonate derivatives, respectively. Fluoride ion mediator can be also applied to anodic intramolecular carbon-carbon coupling to form oxindole and 3-oxotetrahydroisoquinoline derivatives.

Keywords: electrosynthesis using; fluoride ion; ion; ion mediator; organic electrosynthesis

Journal Title: Current Opinion in Electrochemistry
Year Published: 2020

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