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Synthesis 2011(14): 2291-2296  
DOI: 10.1055/s-0030-1260070
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of 1,5-Substituted Anthracenes by Means of Kumada Coupling and Their Derivatization

Sebastian Bringmanna, Saleh A. Ahmedb, Ramona Hartmanna, Jochen Mattay*a
a University of Bielefeld, Organic Chemistry I, Universitätsstraße 25, 33615 Bielefeld, Germany
Fax: +49(521)1066146; e-Mail: mattay@uni-bielefeld.de;
b Assuit University, Chemistry Department, Faculty of Science, 71516 Assuit, Egypt
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Publikationsverlauf

Received 4 April 2011
Publikationsdatum:
30. Juni 2011 (online)

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Abstract

Herein, we present a method to access a series of 1,5-functionalized anthracenes through Kumada coupling. All syntheses start from readily available 1,5-dichloroanthracene. The so-formed anthracenes are further derivatized to enable, for example, attachment to supramolecular systems.

Key words

Grignard reaction - Kumada coupling - cross coupling - anthracene - nickel

    References

  • 1 Fritzsche J. C. R. Hebd. Seances Acad. Sci.  1867,  69:  1035 
    Suche in Google Scholar
  • 2a Becker HD. Chem. Rev.  1993,  93:  145 
    Suche in Google Scholar
  • 2b Bouas-Laurent H. Castellan A. Desvergne J.-P. Lapouyade R. Chem. Soc. Rev.  2000,  29:  43 
    Suche in Google Scholar
  • 2c Bouas-Laurent H. Castellan A. Desvergne J.-P. Lapouyade R. Chem. Soc. Rev.  2001,  30:  248 
    Suche in Google Scholar
  • 3a Zhang G. Zhang D. Ziao X. Ai X. Zhang J. Zhu D. Chem. Eur. J.  2006,  12:  1067 
    Suche in Google Scholar
  • 3b Kim SK. Singh NJ. Kim SJ. Kim HG. Kim JK. Lee JW. Kim KS. Yoon J. Org. Lett.  2003,  5:  2083 
    Suche in Google Scholar
  • 3c Kim YK. Lee HN. Singh NJ. Choi HJ. Xue JY. Kim KS. Yoon J. Hyun MH. J. Org. Chem.  2008,  73:  301 
    Suche in Google Scholar
  • 3d Nishimura G. Maehara H. Shiraishi Y. Hirai T. Chem. Eur. J.  2008,  14:  259 
    Suche in Google Scholar
  • 3e Shirtcliff LD. Xu H. Diederich F. Eur. J. Org. Chem.  2010,  846 
  • 3f Kaanumalle LS. Gibb CLD. Gibb BC. Ramamurthy V. J. Am. Chem. Soc.  2005,  127:  3674 
    Suche in Google Scholar
  • 3g Jayaraj N. Zhao Y. Parthasarathy A. Porel M. Liu RSH. Ramamurthy V. Langmuir  2009,  25:  10575 
    Suche in Google Scholar
  • 3h Tosic O. Mattay J. Eur. J. Org. Chem.  2011,  371 
  • 4a Schäfer C. Eckel R. Ros R. Mattay J. Anselmetti D. J. Am. Chem. Soc.  2007,  129:  1488 
    Suche in Google Scholar
  • 4b Schäfer C. Strübe F. Bringmann S. Mattay J. Photochem. Photobiol. Sci.  2008,  7:  1457 
    Suche in Google Scholar
  • 4c Molard Y. Bassani DM. Desvergne J.-P. Moran N. Tucker JHR. J. Org. Chem.  2006,  71:  8523 
    Suche in Google Scholar
  • 4d Okada M. Harada A. Macromolecules  2003,  36:  9701 
    Suche in Google Scholar
  • 4e Toyota S. Kuga M. Takatsu A. Goichi M. Iwanaga T. Chem. Commun.  2008,  1323 
  • 4f Cao D. Meier H. Angew. Chem. Int. Ed.  2001,  40:  186 ; Angew. Chem. 2001, 113, 193
    Suche in Google Scholar
  • 4g Gassensmith JJ. Baumes JM. Eberhard J. Smith BD. Chem. Commun.  2009,  2517 
  • 4h Gassensmith JJ. Arunkumar E. Barr L. Baumes JM. DiVittorio KM. Johnson JR. Noll BC. Smith BD. J. Am. Chem. Soc.  2007,  129:  15054 
    Suche in Google Scholar
  • 5 Schäfer C. Herrmann F. Mattay J. Beilstein J. Org. Chem.  2008,  4:  41 ; doi: 10.3762/bjoc.4.41
    Suche in Google Scholar
  • 6 Fages F. Desvergne J.-P. Frisch I. Bouas-Laurent H. J. Chem. Soc., Chem. Commun.  1988,  1414 
  • 7a Toyota S. Goichi M. Kotani M. Angew. Chem. Int. Ed.  2004,  43:  2248 ; Angew. Chem. 2004, 116, 2298
    Suche in Google Scholar
  • 7b Vögtle F. Koch H. Rissanen K. Chem. Ber.  1992,  125:  2129 
    Suche in Google Scholar
  • 7c Brettar J. Gisselbrecht J.-P. Gross M. Solladié N. Chem. Commun.  2001,  733 
  • 7d Bar AK. Gole B. Ghosh S. Mukherjee PS. Dalton Trans.  2009,  6701 
  • 7e Ghosh S. Chakrabarty R. Mukherjee PS. Inorg. Chem.  2009,  48:  549 
    Suche in Google Scholar
  • 7f Katz HE. J. Org. Chem.  1989,  54:  2179 
    Suche in Google Scholar
  • 7g Kauffman JM. Synthesis  2001,  197 
  • 7h Effenberger F. Heid S. Merkle R. Zimmermann P. Synthesis  1995,  1115 
  • 7i Yagodkin E. Douglas CJ. Tetrahedron Lett.  2010,  51:  3037 
    Suche in Google Scholar
  • 7j Rein R. Gross M. Solladié N. Chem. Commun.  2004,  1992 
  • 7k Flamingni L. Talarico AM. Ventura B. Rein R. Solladié N. Chem. Eur. J.  2006,  12:  701 
    Suche in Google Scholar
  • 7l House HO. Hrabie JA. VanDerveer D. J. Org. Chem.  1986,  51:  921 
    Suche in Google Scholar
  • 7m

    Synthesis of 1,5-dichloroanthra-cene (1) is analogous to the described synthesis7l of 1,8-dichloroanthracene.

  • 8a Rosen BM. Quasdorf KW. Wilson DA. Zhang N. Resmerita A.-M. Garg NK. Percec V. Chem. Rev.  2011,  111:  1346 
    Suche in Google Scholar
  • 8b Jana R. Pathak TP. Sigman MS. Chem. Rev.  2011,  111:  1417 
    Suche in Google Scholar
  • 9a Clar E. Mackay CC. Tetrahedron  1972,  28:  5049 
    Suche in Google Scholar
  • 9b Cristol SJ. Caspar ML. J. Org. Chem.  1967,  33:  2020 
    Suche in Google Scholar
  • For examples from numerous reports in the literature, see:
  • 10a Martinez GR. Garcia F. Catalani LH. Cadet J. Oliveira MCB. Ronsein GE. Miyamoto S. Medeiros MHG. Di Mascio P. Tetrahedron  2006,  62:  10762 
    Suche in Google Scholar
  • 10b Barton DHR. Hui RAHF. Lester DJ. Ley SV. Tetrahedron Lett.  1979,  3331 
  • 10c Koeberg-Telder A. Cerfontain H. Tetrahedron Lett.  1974,  3535 
  • 10d Tanko JM. Wang Y. Chem. Commun.  1997,  2387 
  • 11a Kitagawa K. Inoue A. Shinokubo H. Oshima K. Angew. Chem. Int. Ed.  2000,  39:  2481 ; Angew. Chem. 2000, 112, 2594
    Suche in Google Scholar
  • 11b Inoue A. Kitagawa K. Shinikubo H. Oshima K. J. Org. Chem.  2001,  66:  4333 
    Suche in Google Scholar
  • 12 Lau SYW. Hughes G. O’Shea PD. Davies IW. Org. Lett.  2007,  9:  2239 
    CrossrefSuche in Google Scholar
  • 13 Cashman JR. Voelker T. Zhang H.-T. O’Donnell JM. J. Med. Chem.  2009,  52:  1530 
    CrossrefSuche in Google Scholar
  • 14 Sakata Y. Toyoda T. Misumi S. Tetrahedron Lett.  1992,  33:  5077 
    CrossrefSuche in Google Scholar
  • 16 Palazzott MC, Rakow NA, and Wendland MS. inventors; Fluorescent chemical sensor, U.S. Pat. Appl. Publ.  G01N 33/50 20060101 G01N033/50. 
  • 17 Osuka A. Fujikane D. Shinmori H. Kobatake S. Irie M. J. Org. Chem.  2001,  66:  3913 
    CrossrefSuche in Google Scholar
15

Bringmann S., Brodbeck R., Hartmann R., Schäfer C., Mattay J. to be published