Download PDF
Synlett 2011(20): 3023-3025  
DOI: 10.1055/s-0031-1289881
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of Dibenzofurans by Palladium-Catalysed Tandem Denitrification/C-H Activation

Zhenting Du*, Jing Zhou, Changmei Si, Weili Ma
College of Science, Northwest A&F University, Yangling, Shaanxi, 712100, P. R. of China
Fax: +86(29)87092226; e-Mail: duzt@nwsuaf.edu.cn;
Further Information

Publication History

Received 30 August 2011
Publication Date:
11 November 2011 (online)

   Permissions and Reprints All articles of this category
Preview

Corrected by:

Synthesis of Dibenzofurans by Palladium-Catalysed Tandem Denitrification/C–H ActivationSynlett 2012; 23(14): 2146-2146
DOI: 10.1055/s-0032-1317174

Abstract

A palladium-catalysed method for intramolecular cyclisation of ortho-diazonium salts of diaryl ethers to give dibenzofurans is described. The protocol uses 3 mol% palladium acetate as the catalyst in refluxing ethanol in the absence of base.

Key words

palladium acetate - dibenzofurans - diazonium salts

    References and notes

  • 1a Kokubun T. Harborne JB. Eagles J. Waterman PG. Phytochemistry  1995,  39:  1033 
    Search in Google Scholar
  • 1b Pagani A. Scala F. Chianese G. Grassi G. Appendino G. Taglialatela-Scafati O. Tetrahedron  2011,  67:  3369 
    Search in Google Scholar
  • 1c Carney JR. Krenisky JM. Williamson RT. Luo J. J. Nat. Prod.  2002,  65:  203 
    Search in Google Scholar
  • 2a De Lombaert S. Blanchard L. Stamford LB. Tan J. Wallace EM. Satoh Y. Fitt J. Hoyer D. Simonsbergen D. Moliterni J. Marcopoulos N. Savage P. Chou M. Trapani AJ. Jeng AY. J. Med. Chem.  2000,  43:  488 
    Search in Google Scholar
  • 2b Kaul R. Deechongkit S. Kelly JW. J. Am. Chem. Soc.  2002,  124:  11900 
    Search in Google Scholar
  • 2c Momotake A. Lindegger N. Niggli E. Barsotti RJ. Ellis-Davies GCR. Nat. Methods  2006,  3:  35 
    Search in Google Scholar
  • 2d Oliveira AMAG. Raposo MMM. Oliveira-Campos AMF. Machado AEH. Puapairoj P. Pedro M. Nascimento MSJ. Portela C. Afonso C. Pinto M. Eur. J. Med. Chem.  2006,  41:  367 
    Search in Google Scholar
  • 3 Bressler DC. Fedorak PM. Can. J. Microbiol.  2000,  46:  397 
    Search in Google Scholar
  • 4a Suzuki H, Suzuki T, and Seo S. inventors; US  20110114928. 
  • 4b Kawaguchi K. Nakano K. Nozaki K. J. Org. Chem.  2007,  72:  5119 
    Search in Google Scholar
  • 5 Komine Y. Kamisawa A. Tanaka K. Org. Lett.  2009,  11:  2361 
    Search in Google Scholar
  • 6a Henderson WA. Zweig A. Tetrahedron Lett.  1969,  625 
  • 6b Bratt J. Suchitzky H. J. Chem. Soc., Chem. Commun.  1972,  949 
  • 7a Ejlx JA. Murphy DPH. Sargent MV. Synth. Commun.  1972,  2:  427 
    Search in Google Scholar
  • 7b Zeller K.-P. Petersen H. Synthesis  1975,  532 
  • 8 Wang J.-Q. Harvey RG. Tetrahedron  2002,  58:  5927 
    Search in Google Scholar
  • 9a Liegault B. Lee D. Huestis MP. Stuart DR. Fagnou K. J. Org. Chem.  2008,  73:  5022 
    Search in Google Scholar
  • 9b Campeau L.-C. Parisien M. Jean A. Fagnou K. J. Am. Chem. Soc.  2005,  128:  581 
    Search in Google Scholar
  • 10a Voutchkova A. Coplin A. Leadbeater NE. Crabtree RH. Chem. Commun.  2008,  6312 
  • 10b Wang C. Piel I. Glorius F. J. Am. Chem. Soc.  2009,  131:  4194 
    Search in Google Scholar
  • 11 Gajera JM. Gopalan B. Yadav PS. Patil SD. Gharat LA. J. Heterocycl. Chem.  2008,  45:  797 
    Search in Google Scholar
  • 12a Graebe C. Ullmann F. Ber. Dtsch. Chem. Ges.  1896,  29:  1876 
    Search in Google Scholar
  • 12b DeTar DF. Org. React. (N.Y.)  1957,  409 
  • 12c Wassmundt FW. Pedemonte RP. J. Org. Chem.  1995,  60:  4991 
    Search in Google Scholar
  • 13a Yamato T. Hideshima C. Prakash GKS. Olah GA. J. Org. Chem.  1991,  56:  3192 
    Search in Google Scholar
  • 13b Petrocelli FP. Klein MT. Ind. Eng. Chem. Prod. Res. Dev.  1985,  24:  635 
    Search in Google Scholar
  • 14 Xiao B. Gong T.-J. Liu Z.-J. Liu J.-H. Luo D.-F. Xu J. Liu L. J. Am. Chem. Soc.  2011,  133:  9250 
    Search in Google Scholar
  • 15a Sierakowski AF. Aust. J. Chem.  1983,  36:  1281 
    Search in Google Scholar
  • 15b Umemoto T. Adachi K. Ishihara S. J. Org. Chem.  2007,  72:  6905 
    Search in Google Scholar
  • 16a Du ZT. Wang Y. Ma WL. Lv D. Yu HR. Nat. Prod. Commun.  2011,  6:  167 
    Search in Google Scholar
  • 16b Du ZT. Yu HR. Xu Y. Song QL. Li AP. J. Chin. Chem. Soc. (Taipei, Taiwan)  2010,  57:  399 
    Search in Google Scholar
  • 16c Du ZT. Xu Y. Yu HR. Li Y. Acta Crystallogr., Sect. E: Struct. Rep. Online  2010,  66:  O415 
    Search in Google Scholar
  • 16d Du ZT. Lu J. Yu HR. Xu Y. Li AP.
    J. Chem. Res.  2010,  222 
  • 16e Du ZT. Li Y. Wang Y. Ding LC. Gao JM. Synth. Commun.  2010,  40:  1920 
    Search in Google Scholar
  • 18 Jiro T. Palladium Reagents and Catalysts: New Perspectives for the 21st Century   Wiley; New York: 2004. 
  • 19 Zeng M. Du Y. Shao L. Qi C. Zhang X.-M. J. Org. Chem.  2010,  75:  2556 
    Search in Google Scholar
17

CCDC 847585 contains the crystallographic data for this paper. These have been deposited with the Cambridge Crystallographic Data Center.

20

General procedure for the preparation of dibenzofurans from ortho-diazonium salts of diaryl ethers using Pd(OAc)2: To a stirred suspension of the ortho-diazonium salt of the appropriate diaryl ether (5 mmol) in EtOH (20 mL), a catalytic amount Pd(OAc)2 (33 mg, 0.15 mmol) was added, and the resulting mixture was heated at reflux for 30-60 min. The precipitate of metal was filtered, the filtrate was evaporated under vacuum, and the crude product was purified by column chromatography on silica gel eluting with a mixture of petroleum ether and EtOAc to give dibenzofurans.

21

Spectral data of compound 2i: ¹H NMR (500 MHz, CDCl3): δ = 7.88 (s, 1 H), 7.53 (d, J = 8.7 Hz, 1 H), 7.48 (d, J = 7.6 Hz, 1 H), 7.41 (d, J = 8.5 Hz, 1 H), 7.28 (t, J = 7.8 Hz, 1 H), 7.01 (δ, J = 7.6 Hz, 1 H), 4.07 (s, 3 H). ¹³C NMR (125 MHz, CDCl3): d = 154.4, 145.9, 145.6, 128.3, 127.2, 125.8, 124.8, 123.8, 120.6, 112.9, 112.8, 109.9, 56.2. IR: 1443, 1296, 1258, 1199, 1105 cm-¹.