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Synlett 2003(12): 1789-1790  
DOI: 10.1055/s-2003-41407
LETTER
© Georg Thieme Verlag Stuttgart · New York

Copper-Catalyzed Cross-Coupling of Aryl Halides and Thiols Using Microwave Heating

Yong-Jin Wu*, Huan He
Department of Neuroscience Chemistry, Bristol-Myers Squibb Pharmaceutical Research Institute, 5 Research Parkway, Wallingford, CT, 06492, USA
Fax: +1(203)6777702; e-Mail: Yong-Jin.Wu@bms.com;
Further Information

Publication History

Received 28 May 2003
Publication Date:
28 August 2003 (online)

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Abstract

The copper-catalyzed cross-coupling of aryl halides and thiols using microwave heating is described.

Key words

copper(I) iodide - copper-catalyzed - cross-coupling - microwave heating - aryl halide

    References

  • 1 Tiecco M. Synthesis  1988,  749 
    Article in Thieme ConnectGoogle Scholar
  • 2 Liu G. Link JT. Pei Z. Reilly EB. Leitza S. Nguyen B. Marsh KC. Okasinski GF. Geldern TW. Ormes M. Fowler K. Gallatin M. J. Med. Chem.  2000,  43:  4025 
    CrossrefGoogle Scholar
  • 3 Wang Y. Chackalamannil S. Hu Z. Clader JW. Greenlee W. Billard W. Binch H. Crosby G. Ruperto V. Duffy R. McQuade R. Lachowicz JE. Bioorg. Med. Chem. Lett.  2000,  10:  2247 
    CrossrefPubMedGoogle Scholar
  • 4 Nagai Y. Irie A. Nakamura H. Hino K. Uno H. Nishimura H. J. Med. Chem.  1982,  25:  1065 
    CrossrefGoogle Scholar
  • 5 Kaldor SW. Kalish VJ. Davies JF. Shetty BV. Fritz JE. Appelt K. Burgess JA. Campanale KM. Chirgadze NY. Clawson DK. Dressman BA. Hatch SD. Khalil DA. Kosa MB. Lubbehusen PP. Muesing MA. Patick AK. Reich SH. Su KS. Tatlock JH. J. Med. Chem.  1997,  40:  3979 
    CrossrefGoogle Scholar
  • 6 Sasaki NA. Hashimoto C. Potier P. Tetrahedron Lett.  1987,  28:  6039 
    CrossrefGoogle Scholar
  • 7 Hickman RJS. Christie BJ. Guy RW. White TJ. Aust. J. Chem.  1985,  38:  899 
    CrossrefGoogle Scholar
  • 8a Li GY. Zheng G. Noonan AF. J. Org. Chem.  2001,  66:  8677 
    CrossrefGoogle Scholar
  • 8b Li GY. Angew. Chem. Int. Ed.  2001,  40:  1513 
    CrossrefGoogle Scholar
  • 8c Schopfer U. Schlapbach A. Tetrahedron  2001,  57:  3069 
    CrossrefGoogle Scholar
  • 8d Ciattini PG. Morera E. Ortar G. Tetrahedron Lett.  1995,  36:  4133 
    CrossrefGoogle Scholar
  • 8e Zheng N. McWilliams JC. Fleitz FJ. Armstrong JD. Volante RP. J. Org. Chem.  1998,  63:  9606 
    CrossrefGoogle Scholar
  • 8f Kosugi M. Ogata T. Terada M. Sano H. Migita T. Bull. Chem. Soc. Jpn.  1985,  58:  3657 
    CrossrefGoogle Scholar
  • 9 Herradura PS. Pendola KA. Guy RK. Org. Lett.  2000,  2:  2019 
    CrossrefPubMedGoogle Scholar
  • 10 Kwong FY. Buchwald SL. Org. Lett.  2002,  4:  3517 
    CrossrefPubMedGoogle Scholar
  • 11 Wu Y. He H. Tetrahedron  2003,  44:  3445 
    Google Scholar
  • 12 For a review, see: Perreux L. Loupy A. Tetrahedron  2001,  57:  9199 
    CrossrefGoogle Scholar
  • 13 For a copper(II)-mediated N-arylation of N-H containing heteroarenes with arylboronic acids under microwave irradiation, see: Combs AP. Saubern S. Rafalski M. Lam PYS. Tetrahedron Lett.  1999,  40:  1623 
    CrossrefGoogle Scholar
  • 14 For a microwave-assisted Goldberg reaction, see: Lange JHM. Hofmeyer LJF. Hout FAS. Osnabrug SJM. Verveer PC. Kruse CG. Feenstra RW. Tetrahedron Lett.  2002,  43:  1101 
    CrossrefGoogle Scholar
  • 15a All new compounds have spectral and analytical data in agreement with the indicated structures. 1-tert-Butyl-4-(phenylthio)benzene: 1H NMR (400 MHz, CDCl3): δ = 1.31 (s, 9 H), 7.15-7.35 (m, 9 H). 13C NMR (100 MHz, CDCl3) : δ (attached H’s) = 31.3 (3), 34.6 (0), 126.3 (1), 126.6 (1), 129.1 (1), 130.3 (1), 131.5 (1), 131.6 (0), 136.7 (0), and 150.6 (0). The spectroscopic data are in full agreement with those described in the literature, see: Nakayama J. Fujita T. Hoshino M. Chem. Lett.  1983,  249 
    Google Scholar