Organic electrosynthesis using a fluoride ion mediator |
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| Authors: | Toshio Fuchigami Shinsuke Inagi |
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| Institution: | 1. Department of Electronic Chemistry, Interdisciplinary Graduate School of Science and Engineering, Tokyo Institute of Technology, 4259 Nagatsuta-cho, Midori-ku, Yokohama, 226-8502, Japan;2. Department of Chemical Science and Engineering, School of Materials and Chemical Technology, Tokyo Institute of Technology, 4259 Nagatsuta-cho, Midori-ku, Yokohama, 226-8502, Japan |
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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 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. |
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| Keywords: | Anodic methoxylation Fluoride ion mediator Cyclization Rearrangement |
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