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Synlett 2011(7): 1023-1027  
DOI: 10.1055/s-0030-1259929
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Palladium-Catalyzed Oxidation and Cyclization of Carbon-Carbon Triple Bonds in Fluorous Media Using Molecular Oxygen

Yanmei Wena,b, Shifa Zhua, Huanfeng Jiang*a, Azhong Wanga, Zhenwang Chena
a School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou 510640, P. R. of China
b College of Science, Guangdong Ocean University, Zhanjiang 524088, P. R. of China
Fax: +86(20)87112906; e-Mail: jianghf@scut.edu.cn;
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Publication History

Received 16 November 2010
Publication Date:
29 March 2011 (online)

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Abstract

An intriguing, facile, and efficient oxidation and cyclization of alkynes catalyzed by Pd(OAc)2 in a fluorous biphasic system of N,N-dimethylacetamide (DMA) and perfluorodecalin directly with molecular oxygen is described, which opens an efficient access to tetrasubstituted furans. Under the optimized conditions, intermolecular reaction between diverse alkynes provides the corresponding mixture of regioisomers with appreciable selectivity. Intramolecular oxidation and cyclization of alkynes are also successfully demonstrated. The reaction proceeds efficiently under mild conditions with atmospheric oxygen as the sole oxidant.

Key words

perfluorodecalin - molecular oxygen - alkynes - palladium-catalyzed - oxidation

    References

  • 1a Mortensen DJ. Rodriguez AL. Carlson KE. Sun J. Katzenellenbogen BS. Katzenellenbogen JA. J. Med. Chem.  2001,  44:  3838 
    Search in Google Scholar
  • 1b Francesconi I. Wilson WD. Tanious FA. Hall JE. Bender BC. Tidwell RR. McCurdy D. Boykin DW. J. Med. Chem.  1999,  42:  2260 
    Search in Google Scholar
  • 1c Rahmathullah SM. Hall JE. Bender BC. McCurdy DR. Tidwell RR. Boykin DW. J. Med. Chem.  1999,  42:  3994 
    Search in Google Scholar
  • 1d Mullican MD. Sorenson RJ. Connor DT. Thueson DO. Kennedy JA. Conroy MC. J. Med. Chem.  1991,  34:  2186 
    Search in Google Scholar
  • 1e Flynn BL. Hamel E. Jung MK. J. Med. Chem.  2002,  45:  2670 
    Search in Google Scholar
  • 1f Giardina D. Crucianelli M. Romanelli R. Leonardi A. Poggesi E. Melchiorre C. J. Med. Chem.  1996,  39:  4602 
    Search in Google Scholar
  • 1g Hopkins KT. Wilson WD. Bender BC. McCurdy DR. Hall JE. Tidwell RR. Kumar A. Bajic M. Boykin DW. J. Med. Chem.  1998,  41:  3872 
    Search in Google Scholar
  • 1h Bolognesi ML. Budriesi R. Chiarini A. Poggesi E. Leonardi A. Melchiorre C. J. Med. Chem.  1998,  41:  4844 
    Search in Google Scholar
  • 1i Cacchi S. J. Organomet. Chem.  1999,  576:  42 
    Search in Google Scholar
  • 1j Hou XL. Cheung HY. Hon TY. Kwan PL. Lo TH. Tong SY. Wong HNC. Tetrahedron  1998,  54:  1955 
    Search in Google Scholar
  • 2a Nishino H. Kajikawa S. Hamada Y. Kurosawa K. Tetrahedron Lett.  1995,  36:  5753 
    Search in Google Scholar
  • 2b Lee H.-K. Chan K.-F. Hui C.-W. Yim H.-K. Wu X.-W. Wong HNC. Pure Appl. Chem.  2005,  77:  139 
    Search in Google Scholar
  • 2c Dean FM. Adv. Heterocycl. Chem.  1982,  30:  167 
    Search in Google Scholar
  • 2d Lipshutz BH. Chem. Rev.  1986,  86:  795 
    Search in Google Scholar
  • 2e Brown TH. Armitage MA. Blakemore RC. Blurton P. Durant GJ. Ganellin CR. Ife RJ. Parsons ME. Rawlings DA. Slingsby BP. Eur. J. Med. Chem.  1990,  217 
  • 3a Onitsuka S. Nishino H. Kurosawa K. Tetrahedron Lett.  2000,  41:  3149 
    Search in Google Scholar
  • 3b Dudnik AS. Sromek AW. Rubina M. Kim JT. Kel’in AV. Gevorgyan V. J. Am. Chem. Soc.  2008,  130:  1440 
    Search in Google Scholar
  • 3c Schwier T. Sromek AW. Yap DML. Chernyak D. Gevorgyan V. J. Am. Chem. Soc.  2007,  129:  9868 
    Search in Google Scholar
  • 3d Peng LL. Zhang X. Ma M. Wang JB. Angew. Chem. Int. Ed.  2007,  46:  1905 
    Search in Google Scholar
  • 3e Sromek AW. Rubina M. Gevorgyan V. J. Am. Chem. Soc.  2005,  127:  10500 
    Search in Google Scholar
  • 3f Xia YZ. Dudnik AS. Gevorgyan V. Li YH. J. Am. Chem. Soc.  2008,  130:  6940 
    Search in Google Scholar
  • 3g Feng X. Tan Z. Chen D. Shen Y. Guo C. Xiang J. Zhu C. Tetrahedron Lett.  2008,  49:  4110 
    Search in Google Scholar
  • 3h Cao H. Jiang H. Mai R. Zhu S. Qia C. Adv. Synth. Catal.  2010,  352:  143 
    Search in Google Scholar
  • 3i Zhang X. Lu Z. Fu C. Ma S. J. Org. Chem.  2010,  75:  2589 
    Search in Google Scholar
  • 3j Brown RCD. Angew. Chem. Int. Ed.  2005,  44:  850 
    Search in Google Scholar
  • 3k Cacchi S. J. Organomet. Chem.  1999,  576:  42 
    Search in Google Scholar
  • 3l Keay BA. Chem. Soc. Rev.  1999,  28:  209 
    Search in Google Scholar
  • 4a Nakano M. Tsurugi H. Satoh T. Miura M. Org. Lett.  2008,  10:  1851 
    Search in Google Scholar
  • 4b Brown RCD. Angew. Chem. Int. Ed.  2005,  44:  850 
    Search in Google Scholar
  • 4c Kirsch SF. Org. Biomol. Chem.  2006,  4:  2076 
    Search in Google Scholar
  • 4d Kawai H. Oi S. Inoue Y. Heterocycles  2006,  67:  101 
    Search in Google Scholar
  • 4e Li Y. Yu Z. J. Org. Chem.  2009,  74:  8904 
    Search in Google Scholar
  • 4f Xiao Y. Zhang JL. Chem. Commun.  2010,  752 
  • 4g Wang T. Zhang J. Dalton Trans.  2010,  39:  4270 
    Search in Google Scholar
  • 4h Dudnik AS. Gevorgyan V. Angew. Chem. Int. Ed.  2007,  46:  5195 
    Search in Google Scholar
  • 4i Fukuda Y. Shiragami H. Utimoto K. Nozaki H. J. Org. Chem.  1991,  56:  5816 
    Search in Google Scholar
  • 4j Sniady A. Wheeler KA. Dembinski R. Org. Lett.  2005,  7:  1769 
    Search in Google Scholar
  • 4k Gabriele B. Salerno G. Lauria E. J. Org. Chem.  1999,  64:  7687 
    Search in Google Scholar
  • 4l Seiller B. Bruneau C. Dixneuf PH. Tetrahedron  1995,  51:  13089 
    Search in Google Scholar
  • 4m Liu Y. Song F. Song Z. Liu M. Yan B. Org. Lett.  2005,  7:  5409 
    Search in Google Scholar
  • 5a Zeni G. Larock RC. Chem. Rev.  2006,  106:  4644 
    Search in Google Scholar
  • 5b Beccalli EM. Broggini G. Martinelli M. Sottocornola S. Chem. Rev.  2007,  107:  5318 
    Search in Google Scholar
  • 5c Chen X. Engle KM. Wang D. Yu J. Angew. Chem. Int. Ed.  2009,  48:  5094 
    Search in Google Scholar
  • 5d Lyons TW. Sanford MS. Chem. Rev.  2010,  110:  1147 
    Search in Google Scholar
  • 6 Wang A. Jiang H. Xu Q. Synlett  2009,  929 
    Thieme Connect
  • 7 Sharts CM. Reese HR. J. Fluorine Chem.  1978,  11:  637 
    CrossrefSearch in Google Scholar
  • 8a Horváth IT. Rábai J. Science  1994,  266:  72 
    Search in Google Scholar
  • 8b DiMagno SG. Dussault PH. Schultz JA. J. Am. Chem. Soc.  1996,  118:  5312 
    Search in Google Scholar
  • 9a Lu N. Lin Y. Tetrahedron Lett.  2007,  48:  8823 
    Search in Google Scholar
  • 9b Betzemeier B. Lhermitte F. Knochel P. Tetrahedron Lett.  1998,  39:  6667 
    Search in Google Scholar
  • 9c Hope EG. Kemmitt RDW. Paige DR. Stuart AM. J. Fluorine Chem.  1999,  99:  197 
    Search in Google Scholar
  • 9d Shen M. Cai C. Yi W. J. Fluorine Chem.  2007,  128:  1421 
    Search in Google Scholar
  • 9e Hao X. Yamazaki O. Yoshida A. Nishikido J. Green Chem.  2003,  5:  524 
    Search in Google Scholar
  • 9f Colonna S. Gaggero N. Montanari F. Pozzi G. Quici S. Eur. J. Org. Chem.  2001,  181 
  • 9g Schneider S. Bannwarth W. Angew. Chem. Int. Ed.  2000,  39:  4142 
    Search in Google Scholar
  • 9h Tesevic V. Gladysz JA. J. Org. Chem.  2006,  71:  7433 
    Search in Google Scholar
  • 9i Contel M. Villuendas PV. Gallardo JF. Alonso PJ. Vincent JM. Fish RH. Inorg. Chem.  2005,  44:  9771 
    Search in Google Scholar
  • 9j Curran DP. Hadida S.
    J. Am. Chem. Soc.  1996,  118:  2531 
    Search in Google Scholar