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Pure Appl. Chem., 2010, Vol. 82, No. 4, pp. 1055-1063

http://dx.doi.org/10.1351/PAC-CON-09-10-21

Published online 2010-03-19

Novel anodic concepts for the selective phenol coupling reaction

Siegfried R. Waldvogel

Rheinische Friedrich-Wilhelms-Universität Bonn; Kekulé Institute for Organic Chemistry and Biochemistry, Gerhard-Domagk-Strasse 1, 53121 Bonn, Germany

References

  • 1. G. Bringmann, C. Günther, M. Ochse, O. Schupp, S. Tasler. Progress in the Chemistry of Organic Natural Products, Vol. 2, W. Herz, H. Falk, G. W. Kirby, R. E. Moore (Eds.) Springer, Vienna (2001).
  • 2a. W. S. Knowles. Adv. Synth. Catal. 345, 3 (2003). (http://dx.doi.org/10.1002/adsc.200390028)
  • 2b. R. Noyori. Adv. Synth. Catal. 345, 15 (2003). (http://dx.doi.org/10.1002/adsc.200390002)
  • 2c. W. S. Knowles. Asymmetric Catalysis on Industrial Scale, H. U. Blaser, E. Schmidt (Eds.), p. 23, Wiley-VCH, Weinheim (2004).
  • 3. 2 in monodentate P(III) ligand systems and applications thereof.
  • 3a. C. Hawner, K. Li, V. Cirriez, A. Alexakis. Angew. Chem., Int. Ed. 47, 8211 (2008). (http://dx.doi.org/10.1002/anie.200803436)
  • 3b. L. Palais, I. S. Mikhel, C. Bournaud, L. Micouin, C. A. Falciola, M. Vuagnoux-d’Augustin, S. Rosset, G. Bernardinelli, A. Alexakis. Angew. Chem., Int. Ed. 46, 7462 (2007). (http://dx.doi.org/10.1002/anie.200702186)
  • 3c. M. Vuagnoux-d’Augustin, S. Kehrli, A. Alexakis. Synlett 2057 (2007).
  • 3d. K. Li, A. Alexakis. Chem.—Eur. J. 13, 3765 (2007). (http://dx.doi.org/10.1002/chem.200601327)
  • 3e. C. A. Falciola, A. Alexakis. Angew. Chem., Int. Ed. 46, 2619 (2007). (http://dx.doi.org/10.1002/anie.200604963)
  • 3f. E. Raluy, M. Dieguez, O. Pamies. J. Org. Chem. 72, 2842 (2007). (http://dx.doi.org/10.1021/jo062311j)
  • 3g. Y. Mata, O. Pimies, M. Dieguez. Chem.—Eur. J. 13, 3296 (2007). (http://dx.doi.org/10.1002/chem.200601714)
  • 3h. A. Alexakis, D. Polet, S. Rosset, S. March. J. Org. Chem. 69, 5660 (2004). (http://dx.doi.org/10.1021/jo049359m)
  • 3i. K. Li, A. Alexakis. Angew. Chem., Int. Ed. 45, 7600 (2006). (http://dx.doi.org/10.1002/anie.200602417)
  • 4. 2 in bidentate PIII ligands and catalysis.
  • 4a. J. M. Garner, C. P. Lenges, R. J. Mc Kinney. PCT Int. Appl. WO 2008008927 (2008).
  • 4b. M. Bartsch, R. Baumann, G. Haderlein, T. Aechtner, J. Scheidel, H. Luyken, P. Pfab, W. Siegel, V. Weiskopf. PCT Int. Appl. WO 2006040023 (2006).
  • 4c. M. Bartsch, R. Baumann, G. Haderlein, M. A. Flores, T. Jungkamp, H. Luyken, J. Scheidel, W. Siegel. PCT Int. Appl. WO 2005042547 (2005).
  • 4d. M. Bartsch, R. Baumann, G. Haderlein, M. A. Flores, T. Jungkamp, H. Luyken, J. Scheidel, W. Siegel, F. Molnar. PCT Int. Appl. WO 2004087314 (2004).
  • 4e. M. Bartsch, R. Baumann, D. P. Kunsmann-Keitel, G. Haderlein, T. Jungkamp, M. Altmayer, W. Siegel, F. Molnar. PCT Int. Appl. WO 2003033142 (2003).
  • 5. Olefin metathesis.
  • 5a. S. Hayano, H. Kurakata, Y. Tsunogae, Y. Nakayama, Y. Sato, H. Yasuda. Macromolecules 36, 7422 (2003). (http://dx.doi.org/10.1021/ma034611y)
  • 5b. R. Singh, C. Czekelius, R. R. Schrock, P. Müller, A. H. Hoveyda. Organometallics 26, 2528 (2007). (http://dx.doi.org/10.1021/om061134+)
  • 5c. A. G. Cortez, R. R. Schrock, A. H. Hoveyda. Angew. Chem., Int. Ed. 46, 4534 (2007). (http://dx.doi.org/10.1002/anie.200605130)
  • 5d. K. C. Hultzsch, J. A. Jernelius, A. H. Hoveyda, R. R. Schrock. Angew. Chem., Int. Ed. 41, 589 (2002). (http://dx.doi.org/10.1002/1521-3773(20020215)41:4<589::AID-ANIE589>3.0.CO;2-V)
  • 5e. A. F. Kiely, J. A. Jernelius, R. R. Schrock, A. H. Hoveyda. J. Am. Chem. Soc. 124, 2868 (2002). (http://dx.doi.org/10.1021/ja012679s)
  • 5f. D. S. La, E. S. Sattely, J. G. Ford, R. R. Schrock, A. H. Hoveyda. J. Am. Chem. Soc. 123, 7767 (2001). (http://dx.doi.org/10.1021/ja010684q)
  • 5g. J. B. Alexander, D. S. La, D. R. Cefalo, A. H. Hoveyda, R. R. Schrock. J. Am. Chem. Soc. 120, 4041 (1998). (http://dx.doi.org/10.1021/ja974353i)
  • 6. G. Lessene, K. S. Feldman. Modern Arene Chemistry, D. Astruc (Ed.), p. 479, Wiley-VCH: Weinheim (2002).
  • 7. A. Nilsson, A. Ronlan, V. D. Parker. J. Chem. Soc., Perkin Trans 1 2337 (1973). (http://dx.doi.org/10.1039/p19730002337)
  • 8a. O. Hoshino. The Alkaloids, Vol. 51, G. A. Cordell (Ed.), p. 323, Academic Press, New York (1998).
  • 8b. S. F. Martin. The Alkaloids, Vol. 30, A. Brossi (Ed.), p. 251, Academic Press, New York (1987).
  • 9. R. B. Herbert. Nat. Prod. Rep. 18, 50 (2001). (http://dx.doi.org/10.1039/a809393h)
  • 10. M. E. Wall, M. C. Wani, F. Fullas, J. B. Oswald, D. M. Brown, T. Santisuk, V. Reutrakul, A. T. McPhail, N. R. Farnsworth. J. Med. Chem. 37, 1465 (1994). (http://dx.doi.org/10.1021/jm00036a012)
  • 11. I. M. Malkowsky. Ph.D. thesis, Bonn University (2006); various electrolyte systems have been applied including different hydroxides or alkoxides in methanol and THF. Best results were reported in [12]. In addition, neutral conditions (0.1 M NBu4BF4 in CH3CN) as well as acidic media (0.1 H2SO4 in methanol) were tested, which lead to a complex electrolysis mixture.
  • 12. I. M. Malkowsky, C. E. Rommel, K. Wedeking, R. Fröhlich, K. Bergander, M. Nieger, C. Quaiser, U. Griesbach, H. Pütter, S. R. Waldvogel. Eur. J. Org. Chem. 241 (2006). (http://dx.doi.org/10.1002/ejoc.200500517)
  • 13. J. Barjau, P. Königs, O. Kataeva, S. R. Waldvogel. Synlett 2309 (2008).
  • 14. J. Barjau, G. Schnakenburg, S. R. Waldvogel. (2009). Manuscript in preparation.
  • 15. S. R. Waldvogel, D. Mirk. Handbook of C–H Transformations G. Dyker (Ed.), p. 251, Wiley-VCH, Weinheim (2005).
  • 16a. M. Schmittel, A. Burghart, W. Malisch, J. Reising, R. Söllner. J. Org. Chem. 63, 396 (1998). (http://dx.doi.org/10.1021/jo971650x)
  • 16b. M. Schmittel, A. Haeuseler. J. Organomet. Chem. 661, 169 (2002). (http://dx.doi.org/10.1016/S0022-328X(02)01823-5)
  • 17a. T. Takada, M. Arisawa, M. Gyoten, R. Hamada, H. Tohma, Y. Kita. J. Org. Chem. 63, 7698 (1998). (http://dx.doi.org/10.1021/jo980704f)
  • 17b. M. Schmittel, A. Haeuseler. Z. Naturforsch. B 58, 211 (2003).
  • 18. F. A. R. Kaul, G. T. Puchta, H. Schneider, M. Grosche, D. Mihalios, W. A. Herrmann. J. Organomet. Chem. 621, 184 (2001). (http://dx.doi.org/10.1016/S0022-328X(00)00861-5)
  • 19. D. Vagedes, R. Fröhlich, G. Erker. Angew. Chem., Int. Ed. 38, 3362 (1999). (http://dx.doi.org/10.1002/(SICI)1521-3773(19991115)38:22<3362::AID-ANIE3362>3.0.CO;2-N)
  • 20a. M. Bishop, S. G. Bott, A. R. Barron. J. Chem. Soc., Dalton Trans. 3100 (2000). (http://dx.doi.org/10.1039/b003375h)
  • 20b. K. G. Caulton, M. H. Chisholm, S. R. Drake, K. Folting, J. C. Huffman, W. Streib. Inorg. Chem. 32, 1970 (1993). (http://dx.doi.org/10.1021/ic00062a016)
  • 20c. R. J. Errington, M. Tombul, G. L. P. Walker, W. Clegg, S. L. Heath, L. Horsburgh. J. Chem. Soc., Dalton Trans. 3533 (1999). (http://dx.doi.org/10.1039/a906089h)
  • 21. I. M. Malkowsky, R. Fröhlich, U. Griesbach, H. Pütter, S. R. Waldvogel. Eur. J. Inorg. Chem. 1690 (2006). (http://dx.doi.org/10.1002/ejic.200600074)
  • 22. I. M. Malkowsky, U. Griesbach, H. Pütter, S. R. Waldvogel. Chem.—Eur. J. 12, 7482 (2006). (http://dx.doi.org/10.1002/chem.200600375)
  • 23. C. E. Rommel, I. M. Malkowsky, S. R. Waldvogel, H. Pütter, U. Griesbach. PCT Int. Appl. WO 2005075709 (2005).
  • 24. S. R. Waldvogel, I. M. Malkowsky, U. Griesbach, H. Pütter, A. Fischer, M. Hahn, R. Kötz. Electrochem. Commun. 11, 1237 (2009). (http://dx.doi.org/10.1016/j.elecom.2009.04.009)
  • 25. U. Griesbach, I. M. Malkowsky, S. R. Waldvogel. Electrochemistry for the Environment, G. Chen, C. Comninellis (Eds.), p. 125, Springer, Berlin (2008).
  • 26. K. E. Carter, J. Farrell. Environ. Sci. Technol. 43, 8350 (2009) and refs. therein. (http://dx.doi.org/10.1021/es9017738)
  • 27. J. Iniesta, P. A. Michaud, M. Panizza, C. Comninellis. Electrochem. Commun. 3, 346, (2001).
  • 28. D. Zollinger, U. Griesbach, H. Pütter, C. Comninellis. Electrochem. Commun. 6, 605 (2004). (http://dx.doi.org/10.1016/j.elecom.2004.04.014)
  • 29a. M. A. Rodrigo, P. A. Michaud, I. Duo, M. Panizza, G. Cerisola, C. Comninellis. J. Electrochem. Soc. 148, D60 (2001). (http://dx.doi.org/10.1149/1.1362545)
  • 29b. M. Panizza, P. A. Michaud, G. Cerisola, C. Comninellis. J. Electroanal. Chem. 507, 206 (2001). (http://dx.doi.org/10.1016/S0022-0728(01)00398-9)
  • 29c. L. Ouattara, I. Duo, T. Diaco, A. Ivandini, K. Honda, T. Rao, A. Fujishima, C. Comninellis. New Diamond Frontier Carbon Technol. 13, 97 (2003).
  • 29d. B. Boye, P. A. Michaud, B. Marselli, M. M. Dieng, E. Brillas, C. Comninellis. New Diamond Frontier Carbon Technol. 12, 63 (2002).
  • 29e. J. F. Zhi, H. B. Wang, T. Nakashima, T. N. Rao, A. Fujishima. J. Phys. Chem. B 107, 13389 (2003). (http://dx.doi.org/10.1021/jp030279g)
  • 29f. B. Boye, E. Brillas, B. Marselli, P. A. Michaud, C. Comninellis, G. Farnia, G. Sandona. Electrochim. Acta 51, 2872 (2006). (http://dx.doi.org/10.1016/j.electacta.2005.08.019)
  • 30. J. Iniesta, P. A. Michaud, M. Panizza, G. Cerisola, A. Aldaz, C. Comninellis. Electrochim. Acta 46, 3573 (2001). (http://dx.doi.org/10.1016/S0013-4686(01)00630-2)
  • 31. I. M. Malkowsky, U. Griesbach, H. Pütter, S. R. Waldvogel. Eur. J. Org. Chem. 4569 (2006). (http://dx.doi.org/10.1002/ejoc.200600466)
  • 32. I. M. Malkowsky, S. R. Waldvogel, H. Pütter, U. Griesbach. PCT Int. Appl. WO 2006077204 (2006).
  • 33. The range can be assumed when free hydroxyl radicals are anticipated and the simulation is based on diffusion-controlled rate for recombination of these radicals.
  • 34a. L. Eberson, M. P. Hartshorn, O. Persson. Angew. Chem., Int. Ed. 34, 2268 (1995).
  • 34b. L. Eberson, M. P. Hartshorn, O. Persson. J. Chem. Soc., Perkin Trans. 2 1735 (1995). (http://dx.doi.org/10.1039/p29950001735)
  • 35. A. Kirste, M. Nieger, I. M. Malkowsky, F. Stecker, A. Fischer, S. R. Waldvogel. Chem.—Eur. J. 15, 2273 (2009). (http://dx.doi.org/10.1002/chem.200802556)
  • 36. A. Kirste, G. Schnakenburg, F. Stecker, A. Fischer, S. R. Waldvogel. Angew. Chem., Int. Ed. 49, 971 (2010). (http://dx.doi.org/10.1002/anie.200904763)