Abstract
The electrochemical oxidation of tetramethoxy precursors (2) to coenzymes Q n (1) at a carbon anode was investigated both in a bench-scale batch electrochemical reactor and in a continuous recirculation reaction system equipped with a parallel-plate electrochemical divided cell. High faradic efficiency (>60%) and excellent selectivity (>90%) in coenzymes Q n were obtained in CH3CN or CH3CN/CH2Cl2 + 0.15 M Bu4NBF4 under potentiostatic or amperostatic alimentation.
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References
Steckhan E (2002) Electrochemistry. In: Ullmann’s encyclopedia of industrial chemistry, 7th edn. Wiley-VCH, Weinheim, Electronic release
Scialdone O, Belfiore C, Filardo G, Galia A, Sabatino MA, Silvestri G (2005) Electrochim Acta 51:598
Putter H (2001) In: Lund H, Hammerich O (eds) Organic electrochemistry, 4th edn. Marcel Dekker, New York, p 1259
Scialdone O, Galia A, Belfiore C, Filardo G, Silvestri G (2004) Ind Eng Chem Res 43:5006
Sabatino MA, Galia A, Filardo G, Scialdone O (2007) Electrochem Commun 9:1355
Filardo G, Galia A, Sabatino MA, Scialdone O (2007) Italian Patent RM2007 A000067
Sinatra ST (2001) In: Kanagan VE, Quinn PJ (eds) Coenzyme Q: molecular mechanism in health and disease. CRC Press, Boca Raton, FL
Shepherd JA, Poon WW, Myles DC, Clarke CF (1996) Tetrahedron Lett 37:2395
Sasaki K, Watanabe M, Suda Y, Ishizuka A, Noparatnaraporn N (2005) J Biosci Bioeng 100:481
Van Liemt WBS, Steggerda WF, Esmeijer R, Lugtenburg J (1994) Recl Trav Chim Pays-Bas 113:153
Lipshutz BH, Bulow G, Fernandez-Lazaro F, Kim SK, Lowe RF, Mollard P, Stevens KL (1999) J Am Chem Soc 121:11664
Min JH, Lee JS, Yang JD, Koo S (2003) J Org Chem 68:7925
West D (2003) United States Patent 6506915
Lipshutz BH, Mollard P, Pfeiffer SS, Chrisman W (2002) J Am Chem Soc 124:14282
Lipshutz BH, Lower A, Berl B, Schein K, Wetterich F (2005) Org Lett 78:4095
Negishi E, Liou SY, Xu C, Huo S (2002) Org Lett 4:261
Sigma-Aldrich Catalog (2006) Sigma-Aldrich, St. Louis, p 682
Wheeler JW, Chung RH (1969) J Org Chem 34:1148
Scialdone O, Filardo G, Galia A, Mantione D, Silvestri G (1999) Acta Chem Scand 53:800
Acknowledgements
This work was financially supported by the Università di Palermo and by the Ministero dell’Istruzione, dell’Università e della Ricerca (MIUR). Antonina Natoli is gratefully acknowledged for her support.
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Sabatino, M.A., Filardo, G., Galia, A. et al. Electrochemical synthesis of coenzymes Q n by oxidation of tetramethoxy precursors. J Appl Electrochem 39, 2529–2533 (2009). https://doi.org/10.1007/s10800-009-9947-6
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DOI: https://doi.org/10.1007/s10800-009-9947-6