Introduction
Much of modern synthetic organic chemistry involves trapping short-lived reaction intermediates in known chemical reactions in order to divert reactions into other paths producing different products. Electrochemistry is ideally suited for this purpose because single electrons are generally transferred to or from the working electrode. The initial intermediate in most organic electrode reactions is an ion radical; the initial reduction step affords an anion radical and the initial oxidation step, a cation radical. Both types of species are quite reactive and often undergo rapid follow-up chemical reactions to afford neutral radicals, as shown in Fig. 1 [1, 2].
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References
Fry AJ (1989) Synthetic organic electrochemistry, vol 2. Wiley, New York
Lund H, Baizer MM (eds) (1991) Organic electrochemistry, 3rd edn. Dekker, New York
Reddy SHK, Chiba Sun YK, Moeller KD (2001) Anodic oxidation of electron-rich olefins: radical cation approaches to the synthesis of bridged bicyclic systems. Tetrahedron 57:5183–5197
New DG, Tesfai Z, Moeller KD (1996) Intramolecular anodic olefin coupling and the use of electron-rich aryl rings. J Org Chem 61:1578–1598
Xu H-C, Moeller KD (2010) Intramolecular hydroamination of dithioketene acetals: an easy route to cyclic amino acid derivatives. Org Lett 12:5174–5177
Sainsbury M, Wyatt J (1976) Intramolecular coupling of diaryl amides by anodic oxidation. J Chem Soc Perkin Trans 1:661–664
Kotani E, Takeuchi N, Tobinaga S (1973) Total synthesis of the alkaloids (+)-oxocrinine and (+)-maritidine by anodic oxidation. Chem Commun 550–551
Yoshida J-i, Suga S (2002) Basic concepts of “cation pool” and “cation flow” methods and their applicatons in conventional and combinatorial organic synthesis. Chem Eur J 8:2650–2658
Shono T, Matsumura Y, Kanazawa T (1983) Electroorganic chemistry. 69. A general method for the synthesis of indoles bearing a variety of substituents at the b-position, and its appication to the synthesis of l-tryptophan. Tetrahedron Lett 24:1259–1262
Shono T, Matsumura Y, Inoue K (1983) Electroorganic chemistry. 71. Anodic a-methoxylation of N-carbomethoxylated or N-acylated a-aminoacid esters and aamino-b-lactams. J Org Chem 48:1388–1389
Wawzonek S, Blaha EW, Berkey R, Runner ME (1955) Polarographic studies in acetonitrile and dimethylformamide. II. Behavior of aromatic olefins and hydrocarbons. J Electrochem Soc 102:235–242
Waldvogel SR, Mentizi S, Kirste A (2012) Boron-doped diamond electrodes for electroorganic synthesis. Topics Curr Chem 320:1–32
Fumihiro A, Hidyuki M, Keishi F, Tsuneo K, Chiaki K, Fuchigami T, Atobe M (2011) Product selectivity control induced by using liquid-liquid parallel laminar flow in a microreactor. Org Biomol Chem 9:4256–4265
Anderson LA, Redden A, Moeller KD (2011) Connecting the dots: using sunlight to drive electrochemical oxidations. Green Chem 13:1652–1654
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Fry, A.J. (2014). Electrogenerated Reactive Species. In: Kreysa, G., Ota, Ki., Savinell, R.F. (eds) Encyclopedia of Applied Electrochemistry. Springer, New York, NY. https://doi.org/10.1007/978-1-4419-6996-5_355
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