Download PDF
Synlett 2011(11): 1567-1572  
DOI: 10.1055/s-0030-1260794
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Facile Synthesis of 2,3-Dihydrobenzofuran-3-ylacetic Acids by Novel Electrochemical Sequential Aryl Radical Cyclization-Carboxylation of 2-Allyloxybromobenzenes Using Methyl 4-tert-Butylbenzoate as an Electron-Transfer Mediator

Hisanori Senboku*, Jun-ya Michinishi, Shoji Hara
Laboratory of Organic Reaction, Division of Chemical Process Engineering, Graduate School of Engineering, Hokkaido University, Sapporo, Hokkaido 060-8628, Japan
Fax: +81(11)7066555; e-Mail: senboku@eng.hokudai.ac.jp;
Further Information

Publication History

Received 29 March 2011
Publication Date:
15 June 2011 (online)

    Permissions and Reprints All articles of this category

Abstract

Facile synthesis of 2,3-dihydrobenzofuran-3-ylacetic acids and related analogues was successfully carried out by a novel electrochemical aryl radical generation and its 5-exo cyclization followed by a carboxylation sequence of 2-allyloxybromobenzenes by using methyl 4-tert-butylbenzoate as an electron-transfer mediator.

Key words

electrochemical reduction - radical cyclization - fixation of carbon dioxide - radical-anion tandem reaction - 2,3-dihydrobenzofuran-3-ylacetic acids

    References and Notes

  • 1a Grimshaw J. Trocha-Grimshaw J. Tetrahedron Lett.  1974,  15:  993 
    Google Scholar
  • 1b Grimshaw J. Haslett RJ. Trocha-Grimshaw J. J. Chem. Soc., Perkin Trans. 1  1977,  2448 
    Google Scholar
  • 1c Grimshaw J. Mannus D. J. Chem. Soc., Perkin Trans. 1  1977,  2456 
    Google Scholar
  • 1d Grimshaw J. Hamilton R. Trocha-Grimshaw J. J. Chem. Soc., Perkin Trans. 1  1982,  229 
    Google Scholar
  • 1e Donnelly S. Grimshaw J. Trocha-Grimshaw J. J. Chem. Soc., Chem. Commun.  1994,  2171 
    Google Scholar
  • 2 LeStrat F. Murphy JA. Hughes M. Org. Lett.  2002,  4:  2735 
    CrossrefGoogle Scholar
  • 3a Ozaki S. Matsushita H. Ohmori H. J. Chem. Soc., Chem. Commun.  1992,  1120 
    Google Scholar
  • 3b Ozaki S. Matsushita H. Ohmori H. J. Chem. Soc., Perkin Trans. 1  1993,  2339 
    Google Scholar
  • 3c Ozaki S. Horiguchi J. Matsushita H. Ohmori H. Tetrahedron Lett.  1994,  35:  725 
    Google Scholar
  • 4 Ihara M. Katsumata A. Setsu F. Tokunaga Y. Fukumoto K. J. Org. Chem.  1996,  61:  677 
    CrossrefGoogle Scholar
  • 5a Olivero S. Clinet JC. Duñach E. Tetrahedron Lett.  1995,  36:  4429 
    Google Scholar
  • 5b Clinet JC. Duñach E. J. Organomet. Chem.  1995,  503:  C48 
    Google Scholar
  • 5c Gómez M. Muller G. Penyella D. Rocamora M. Duñach E. Olivero S. Clinet JC. Organometallics  1997,  16:  5900 
    Google Scholar
  • 5d Olivero S. Rolland JP. Dunãch E. Organometallics  1998,  17:  3747 
    Google Scholar
  • 6a Torii S. Inokuchi T. Yukawa T. J. Org. Chem.  1985,  50:  5875 
    Google Scholar
  • 6b Inokuchi T. Kawafuchi H. Aoki K. Yoshida A. Torii S. Bull. Chem. Soc. Jpn.  1994,  67:  595 
    Google Scholar
  • 7 Munusamy R. Dhathathreyan KS. Balasubramanian KK. Venkatachalam CH. J. Chem. Soc., Perkin Trans. 2  2001,  1154 
    Google Scholar
  • 8a Kurono N. Honda E. Komatsu F. Orito K. Tokuda M. Chem. Lett.  2003,  32:  720 
    Google Scholar
  • 8b Kurono N. Honda E. Komatsu F. Orito K. Tokuda M. Tetrahedron  2004,  60:  1791 
    Google Scholar
  • At the present stage, they concluded that 9,9-diethylfluorene does not work as a ‘typical’ mediator in their electro-reductive radical generation.9d See:
  • 9a

    Nakagawa, Y.; Mitsudo, K.; Tanaka, H. The 89 th Annual Meeting of the Chemical Society of Japan Funabashi, March 27th-30th, 2009, Abstr. No. 1F4-34.

    Google Scholar
  • 9b

    Mitsudo, K.; Nakagawa, Y.; Tanaka, H. The 216 th Electrochemical Society Meeting Vienna, Austria, Oct. 4th-9th, 2009, Abstr. No. 1644.

    Google Scholar
  • 9c

    Mizukawa, Z.; Nakagawa, Y.; Mitsudo, K.; Tanaka, H.; The 77 th Annual Meeting of the Electrochemical Society of Japan Toyama, March 29th-31st, 2010, Abstr. No. 1J08.

    Google Scholar
  • 9d

    Mitsudo, J.; Nakagawa, Y.; Mizukawa, J.; Suga, S.; Akaba, R.; Tanaka, H. The 217 th Electrochemical Society Meeting Vancouver, BC, Canada, April 25th-30th, 2010, Abstr. No. 818.

    Google Scholar
  • 10 Molander GA. Harris CR. Chem. Rev.  1996,  96:  307 
    Google Scholar
  • Representative papers:
  • 11a Curran DP. Totleben MJ. J. Am. Chem. Soc.  1992,  114:  6050 
    Google Scholar
  • 11b Molander GA. McKie JA. J. Org. Chem.  1992,  57:  3132 
    Google Scholar
  • 11c Nomoto A. Koji Y. Shiino G. Tomisaka Y. Mitani I. Tatsumi M. Ogawa A. Tetrahedron Lett.  2010,  51:  6580 
    Google Scholar
  • 12 Olivero S. Duñach E. Eur. J. Org. Chem.  1999,  1885 
    Google Scholar
  • Recent papers:
  • 13a Senboku H. Yamauchi Y. Fukuhara T. Hara S. Electrochemistry  2006,  74:  612 
    Google Scholar
  • 13b Senboku H. Takahashi M. Fukuhara T. Hara S. Chem. Lett.  2007,  36:  228 
    Google Scholar
  • 13c Yamauchi Y. Fukuhara T. Hara S. Senboku H. Synlett  2008,  438 
    Google Scholar
  • 13d Yamauchi Y. Sakai K. Fukuhara T. Hara S. Senboku H. Synthesis  2009,  3375 
    Google Scholar
  • 13e Yamauchi Y. Hara S. Senboku H. Tetrahedron  2010,  66:  473 
    Google Scholar
  • 13f Senboku H. Nakahara K. Fukuhara T. Hara S. Tetrahedron Lett.  2010,  51:  435 
    Google Scholar
  • 13g Ohkoshi M. Michinishi J. Hara S. Senboku H. Tetrahedron  2010,  66:  7732 
    Google Scholar
  • 15 Maekawa H. Murakami T. Miyazaki T. Nishiguchi I. Chem. Lett.  2011,  40:  368 ; and references cited therein
    CrossrefGoogle Scholar
  • 16a Silvestri G. Gambino S. Filardo G. Gulotta A. Angew. Chem., Int. Ed. Engl.  1984,  23:  979 
    Google Scholar
  • 16b Silvestri G. Gambino S. Filardo G. Acta Chem. Scand.  1991,  45:  987 
    Google Scholar
  • 17a Sock O. Troupel M. Périchon J. Tetrahedron Lett.  1985,  26:  1509 
    Google Scholar
  • 17b Chaussard J. Folest JC. Nédélec JY. Périchon J. Sibille S. Troupel M. Synthesis  1990,  369 
    Google Scholar
14

See Supporting Information.