View More View Less
  • 1 Department of Electronic Chemistry, Tokyo Institute of Technology, 4259 Nagatsuta-cho, Midori-ku, Yokohama, 226-8502, Japan
  • 2 Department of Environment and System Sciences, Yokohama National University, 79-7 Tokiwadai, Hodogaya-ku, Yokohama, 240-8501, Japan
Restricted access

Abstract

We have successfully demonstrated that a microflow reactor is extremely useful in controlling reactions involving an unstable o-benzoquinone. As a model reaction, Michael addition reaction between o-benzoquinone generated from electrochemical oxidation of catechol and benzenethiols was employed. This reaction system enables selective oxidation of catechol avoiding the oxidation of benzenethiol, although these oxidation potentials are close to each other. The examination of several reaction conditions indicated that the key features of the method are an effective o-benzoquinone generation and its rapid use for the following reaction without decomposition in a microflow system. In addition, cyclic voltammetry measurements elucidated that catechol concentration and selection of anode material were crucial factors for effective o-quinone generation.

  • 1. (a) Kim, H.; Nagaki, A.; Yoshida, J. Nat. Commun. 2011, 2, 264;

    (b)Yoshida, J. Chem. Record., 2010, 10, 332341.

  • 2. (a) Horii, D.; Fuchigami, T.; Atobe, M. J. Am. Chem. Soc. 2007, 129, 11692;

    (b)Horii, D.; Amemiya, F.; Fuchigami, T.; Atobe, M. Chem. Eur. J. 2008, 14, 10382;

    (c)Amemiya, F.; Fuse, K.; Fuchigami, T.; Atobe, M. Chem. Commun. 2010, 46, 2730;

    (d)Amemiya, F.; Matsumoto, H.; Fuse, K.; Kashiwagi, T.; Kuroda, C.; Fuchigami, T.; Atobe, M. Org. Biomol. Chem. 2011, 9, 4256.

  • 3. Lund, H.; Hammerich, O. Organic Electrochemistry, Marcel Dekker Inc.: New York, 2001.

  • 4. (a) Yoshida, J.; Suga, S.; Suzuki, S.; Kinomura, N.; Yamamoto, A.; Fujiwara, K. J. Am. Chem. Soc. 1999, 121, 9546;

    (b) Morofuji, T.; Shimizu, A.; Yoshida, J. Angew. Chem. Int. Ed. 2012, 51, 7259;

    (c) Sugawara, M.; Mori, K.; Yoshida, J. Electrochim. Acta. 1997, 42, 1995;

    (d) Kim, S.; Hayashi, K.; Kitano, Y.; Tada, M.; Chiba, K. Org. Lett. 2002, 4, 3735.

  • 5. T. Ka shiwagi F. Amemiya F. Fuchigami M. Atobe 2012 Chem. Commun. 48 2806.

  • 6. Booth, J.; Boyland, E.; Turner, E. E. J. Chem. Soc. 1950, 1188.

  • 7. W. A. Pieken J. W. Kozarich 1989 J. Org. Chem. 54 510.

  • 8. (a) Danishefsky, S. J.; Mazza, S. J. Org. Chem. 1974, 39, 3610;

    (b) Paquet, J.; Brassard, P. Can. J. Chem. 1989, 67, 1354;

    (c) Lee, J.; Snyder, J. K. J. Org. Chem. 1990, 55, 4995;

    (d) Lee, J.; Li, J.-H.; Oya, S.; Snyder, J. K. J. Org. Chem. 1992, 57, 5301;

    (e) Nair, V.; Maliakal, D.; Treesa, P. M.; Rath, N. P.; Eigendorf, G. K. Synthesis 2000, 850;

    (f) Abraham, C. J.; Paull, D. H.; Bekele, T.; Scerba, M. T.; Dudding, T.; Lectka, T. J. Am. Chem. Soc. 2008, 130, 17085.

  • 9. (a) Takuwa, A.; Kai, R.; Kawasaki, K.-I.; Nishigaichi, Y.; Iwamoto, H. J. Chem. Soc., Chem. Commun. 1996, 703;

    (b) Nair, V.; Nair, J. S.; Vinod, A. U.; Rath, N. P. J. Chem. Soc. Perkin Trans. 1 1997, 21, 3129;

    (c) Nair, V.; Sheela, K. C.; Radhakrishnan, K. V.; Rath, N. P. Tetrahedron Lett. 1998, 39, 5627;

    (d) Nebois, P.; Fillion, H. Heterocycles 1999, 50, 1137.

  • 10. L. Viallon O. Reinaud P. Capdevielle M. Maumy 1995 Tetrahedron Lett. 36 6669.

  • 11. Kundu, N. G. J. Chem. Soc., Chem. Commun. 1979, 564.

  • 12. F. H. Osman F. A. El-Samahy 2002 Chem. Rev. 102 629.

  • 13. Suzuki, Y.; Matano, H. J. Chem. Soc., Chem. Commun. 1996, 2697.

  • 14. S. Itoh K. Nii M. Mure Y. Ohshiro 1972 Tetrahedron Lett. 34 3975.

  • 15. Balch, A. L.; Sohn, Y. S. J. Organomet. Chem. 1971, C31.

  • 16. H. W. Moore K. F. West U. Wriede K. Chow M. Fernandez N. G. Nguyen 1987 J. Org. Chem. 52 2537.

  • 17. (a) Maruyama, K.; Takuwa, A.; Naruta, Y.; Satao, K.; Soga, O. Chem. Lett. 1981, 47;

    (b)A. Takuwa; O. Soga; T. Mishima; K. Maruyama. J. Org. Chem. 1987, 52, 1261.

  • 18. Sagawa, Y.; Kobayashi, S.; Mukaiyama, T. Chem. Lett. 1988, 1105.

  • 19. (a) Wanzlick, H. W. Angew. Chem. Int. Edit. 1964, 3, 401;

    (b) Jung, M. E.; Perez, F. Org. Lett. 2009, 11, 2165.

  • 20. (a) Fakhari, A. R.; Nematollahi, D.; Shamsipur, M.; Makarem, S.; Davarani, S. S. H.; Alizadeh, A.; Khavasi, H. Tetrahedron 2007, 63, 3894;

    • Search Google Scholar
    • Export Citation

    (b) Nematollahi, D.; Habibi, D.; Rahmati, M.; Rafiee, M. J. Org. Chem. 2004, 69, 2637;

    (c) Nematollahi, D.; Tammari, E. J. Org. Chem. 2005, 70, 7769;

    (d) Zeng, C.-C.; Liu, F.-J.; Ping, D.-W.; Cai, Y.-L.; Zhong, R.-G.; Becker, J. Y. J. Electroanal. Chem. 2009, 625, 131;

    (e) Golabi, S. M.; Nematollahi, D. J. Electroanal. Chem. 1997, 420, 127.

  • 21. (a) Nematollahi, D.; Rafiee, M.; Samadi-Maybodi, A. Electrochim. Acta., 2004, 49, 2495;

    (b) Ansell, M. F.; Gosden, A. F. Chem. Commun. 1965, 21, 520;

    (c) Voisin, E.; William, V. E. Macromolecules 2008, 41, 2994;

    (d) Ryan, M. D.; Yueh, A.; Chen, W.-Y. J. Electrochem. Soc. 1980, 127, 1489.