Download PDF
Synthesis 2010(21): 3602-3608  
DOI: 10.1055/s-0030-1258234
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Efficient Copper-Catalyzed S-Arylation of Thiols with Aryl Bromides and Chlorides

Yaming Li*, Xiaoying Li, Huifeng Wang, Tao Chen, Yusheng Xie
State Key Laboratory of Fine Chemicals, School of Chemical Engineering, Dalian University of Technology, Dalian 116012, P. R. of China
Fax: +86(411)39893900; e-Mail: yamingli@chem.dlut.edu.cn;
Further Information

Publication History

Received 8 June 2010
Publication Date:
30 August 2010 (online)

    Permissions and Reprints All articles of this category

Abstract

An efficient copper-catalyzed system for C-S cross-coupling­ of aromatic thiols with aryl bromides and chlorides has been developed using 1,2,3,4-tetrahydroquinoline-8-ol as a ligand. It is noteworthy that this method is proved to be especially effective for aryl bromides with electron-donating groups. By this protocol, a variety of thioethers as well as symmetrical and unsymmetrical bis-thioethers are obtained in excellent yields with an exceptional level of functional group tolerance and high chemoselectivity.

Key words

copper catalyst - aryl bromides - aryl chlorides - cross-coupling - organic sulfides

    References

  • 1a Liu LP. Stelmach JE. Natarajan SR. Chen MH. Singh SB. Schwartz CD. Fitzgerald CE. O’Keefe SJ. Zaller DM. Schmatz DM. Doherty JB. Bioorg. Med. Chem. Lett.  2003,  13:  3979 
    Google Scholar
  • 1b Procter DJ. J. Chem. Soc., Perkin Trans. 1  2000,  835 
    Google Scholar
  • 1c Procter DJ. J. Chem. Soc., Perkin Trans. 1  2001,  335 
    Google Scholar
  • 1d Corbet JP. Mignani G. Chem. Rev.  2006,  106:  2651 
    Google Scholar
  • 2 De Martino G. Edler MC. La Regina G. Coluccia A. Barbera MC. Barrow D. Nicholson RI. Chiosis G. Brancale A. Hamel E. Artico M. Silvestri R. J. Med. Chem.  2006,  49:  947 
    CrossrefGoogle Scholar
  • 3 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
  • 4a Migita T. Shimizu T. Asami Y. Shiobara J. Kato Y. Kosugi M. Bull. Chem. Soc. Jpn.  1980,  53:  1385 
    Google Scholar
  • 4b Kosugi M. Ogata T. Terada M. Sano H. Migita T. Bull. Chem. Soc. Jpn.  1985,  58:  3657 
    Google Scholar
  • 5a Mann G. Baranano D. Hartwig JF. Rheingold AL. Guzei IA. J. Am. Chem. Soc.  1998,  120:  9205 
    Google Scholar
  • 5b Li GY. Angew. Chem. Int. Ed.  2001,  40:  1513 
    Google Scholar
  • 5c Itoh T. Mase T. Org. Lett.  2004,  6:  4587 
    Google Scholar
  • 5d Fernandez-Rodriguez MA. Shen QL. Hartwig JF. J. Am. Chem. Soc.  2006,  128:  2180 
    Google Scholar
  • 5e Fukuzawa S. Tanihara D. Kikuchi S. Synlett  2006,  2145 
    Google Scholar
  • 5f Eichman CC. Stambuli JP. J. Org. Chem.  2009,  74:  4005 
    Google Scholar
  • 5g Fernandez-Rodriguez MA. Hartwig JF. J. Org. Chem.  2009,  74:  1663 
    Google Scholar
  • 6a Cristau HJ. Chabaud B. Chene A. Christol H. Synthesis  1981,  892 
    Google Scholar
  • 6b Millois C. Diaz P. Org. Lett.  2000,  2:  1705 
    Google Scholar
  • 6c Zhang YG. Ngeow KC. Ying JY. Org. Lett.  2007,  9:  3495 
    Google Scholar
  • 6d Cao YQ. Zhang Z. Guo YX. Wu GQ. Synth. Commun.  2008,  38:  1325 
    Google Scholar
  • 7 Wong YC. Jayanth TT. Cheng CH. Org. Lett.  2006,  8:  5613 
    CrossrefPubMedGoogle Scholar
  • 8a Kwong FY. Buchwald SL. Org. Lett.  2002,  4:  3517 
    Google Scholar
  • 8b Wu YJ. He H. Synlett  2003,  1789 
    Google Scholar
  • 8c Bates CG. Saejueng P. Doherty MQ. Venkataraman D. Org. Lett.  2004,  6:  5005 
    Google Scholar
  • 8d Chen YJ. Chen HH. Org. Lett.  2006,  8:  5609 
    Google Scholar
  • 8e Zhang H. Cao WG. Ma DW. Synth. Commun.  2007,  37:  25 
    Google Scholar
  • 8f Sperotto E. van Klink GPM. de Vries JG. van Koten G. J. Org. Chem.  2008,  73:  5625 
    Google Scholar
  • 9a Reddy VP. Kumar AV. Swapna K. Rao KR. Org. Lett.  2009,  11:  1697 
    Google Scholar
  • 9b Reddy VP. Swapna K. Kumar AV. Rao KR. J. Org. Chem.  2009,  74:  3189 
    Google Scholar
  • 10a Xu HJ. Zhao XY. Deng J. Fu Y. Feng YS. Tetrahedron Lett.  2009,  50:  434 
    Google Scholar
  • 10b Prasad DJC. Naidu AB. Sekar G. Tetrahedron Lett.  2009,  50:  1411 
    Google Scholar
  • 10c Ku X. Huang H. Jiang HL. Liu H. J. Comb. Chem.  2009,  11:  338 
    Google Scholar
  • 10d Bhadra S. Sreedhar B. Ranu BC. Adv. Synth. Catal.  2009,  351:  2369 
    Google Scholar
  • 10e Rout L. Sen TK. Punniyamurthy T. Angew. Chem. Int. Ed.  2007,  46:  5583 
    Google Scholar
  • 10f Deng W. Zou Y. Wang YF. Liu L. Guo QX. Synlett  2004,  1254 
    Google Scholar
  • 10g Jammi S. Sakthivel S. Rout L. Mukherjee T. Mandal S. Mitra R. Saha P. Punniyamurthy T. J. Org. Chem.  2009,  74:  1971 
    Google Scholar
  • 10h Xu HJ. Zhao XY. Fu Y. Feng YS. Synlett  2008,  3063 
    Google Scholar
  • 11 Herrero MT. SanMartin R. Dominguez E. Tetrahedron  2009,  65:  1500 
    CrossrefGoogle Scholar
  • 12 Feng Y. Wang HF. Sun FF. Li YM. Fu XM. Jin K. Tetrahedron  2009,  65:  9737 
    CrossrefGoogle Scholar
  • 13 Chakraborti AK. Sharma L. Nayak MK. J. Org. Chem.  2002,  67:  6406 
    CrossrefGoogle Scholar
  • 14 Akkilagunta VK. Reddy VP. Rao KR. Synlett  2010,  1260 
    Article in Thieme ConnectGoogle Scholar
  • 15a Goyot O. Gingras M. Tetrahedron Lett.  2009,  50:  1977 
    Google Scholar
  • 15b Nakayama J. Katano N. Shimura Y. Sugihara Y. Ishii A. J. Org. Chem.  1996,  61:  7608 
    Google Scholar
  • 16 Wang HF. Li YM. Sun FF. Feng Y. Jin K. Wang XN. J. Org. Chem.  2008,  73:  8639 
    CrossrefPubMedGoogle Scholar
  • 17 Bates CG. Gujadhur RK. Venkataraman D. Org. Lett.  2002,  4:  2803 
    CrossrefPubMedGoogle Scholar
  • 18 Marcincallefebvre A. Gesquiere JC. Lemer C. Dupuis B. J. Med. Chem.  1981,  24:  889 
    CrossrefGoogle Scholar
  • 19a Fernandez-Rodriguez MA. Shen QL. Hartwig JF. Chem. Eur. J.  2006,  12:  7782 
    Google Scholar
  • 19b Sindelar K. Sedivy Z. Hrubantova M. Valchar M. Metysova J. Protiva M. Collect. Czech. Chem. Commun.  1988,  53:  381 
    Google Scholar
  • 20 Lee JY. Lee PH. J. Org. Chem.  2008,  73:  7413 
    CrossrefPubMedGoogle Scholar
  • 21 Clark RD. Jahangir A. Severance D. Salazar R. Chang T. Chang D. Jett MF. Smith S. Bley K. Bioorg. Med. Chem. Lett.  2004,  14:  1053 
    CrossrefGoogle Scholar
  • 22 Allen JV. Bower JF. Williams JMJ. Tetrahedron: Asymmetry  1994,  5:  1895 
    CrossrefGoogle Scholar
  • 23 Vicente J. Abad JA. Lopez-Nicolas RM. Tetrahedron  2008,  64:  6281 
    CrossrefGoogle Scholar
  • 24 Bunnett JF. Creary X. J. Org. Chem.  1974,  39:  3611 
    CrossrefGoogle Scholar
  • 25a Kato T. Kuniyasu H. Kajiura T. Minami Y. Ohtaka A. Kinomoto M. Terao J. Kurosawa H. Kambe N. Chem. Commun.  2006,  868 
    Google Scholar
  • 25b Bourgeois E. Fouassin A. Bull. Soc. Chim. Fr.  1911,  9:  941 
    Google Scholar
  • 26a Petrillo G. Novi M. Garbarino G. Dellerba C. Tetrahedron  1986,  42:  4007 
    Google Scholar
  • 26b Voronkov M. G. Deryagina E. N. Klochkova L. G. Ivanova G. M. Zh. Org. Khim.  1977,  13:  2575 
    Google Scholar