PDF herunterladen
Synthesis 2009(10): 1732-1738  
DOI: 10.1055/s-0029-1216644
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Catalyst-Free and Base-Free Water-Promoted SNAr Reaction of Heteroaryl Halides with Thiols

B. Sreedhar*, P. Surendra Reddy, M. Amarnath Reddy
Inorganic and Physical Chemistry Division, Indian Institute of Chemical Technology, Hyderabad 500007, India
Fax: +91(40)27160921; e-Mail: sreedharb@iict.res.in;
Weitere Informationen

Publikationsverlauf

Received 12 January 2009
Publikationsdatum:
14. April 2009 (online)

   Lizenzen und Reprints Alle Artikel dieser Rubrik
Preview

Abstract

A simple and efficient route for the synthesis of biaryl sulfides have been developed in aqueous medium under base- and catalyst-free conditions. A wide variety of heteroaryl halides and thiols underwent SNAr reaction to provide diaryl sulfides in good to excellent yields. The remarkable key features of the reaction include the use of water as an inexpensive and environmentally benign reaction medium, absence of any additional reagent or catalyst, and easy isolation of the products.

Key words

heteroaryl halides - thiophenol - SNAr reaction - water - 2-thiopyridines

    References

  • 1a Ma X. Gang DR. Nat. Prod. Rep.  2004,  21:  752 
    Suche in Google Scholar
  • 1b Nayyar A. Jain R. Curr. Med. Chem.  2005,  12:  1873 
    Suche in Google Scholar
  • 1c Wishka DG. Graber DR. Kopta LA. Olmsted RA. Friis JM. Hosley JD. Adams WJ. Seest EP. Castle TM. Dolak LA. Keiser BJ. Yagi Y. Jeganathan A. Schlachter ST. Murphy MJ. Cleek GJ. Nugent RA. Poppe SM. Swaney SM. Han F. Watt W. White WL. Poel T.-J. Thomas RC. Voorman RL. Stefanski KJ. Stehle RG. Tarpley WG. Morris J. J. Med. Chem.  1998,  41:  1357 
    Suche in Google Scholar
  • 1d Pathak AK. Pathak V. Seitz LE. Suling WJ. Reynolds RC. J. Med. Chem.  2004,  47:  273 
    Suche in Google Scholar
  • 2 Lowe JA. Qian W. Drozda SE. Volkmann RA. Nason D. Nelson RB. Nolan C. Liston D. Ward K. Faraci S. Verdries K. Seymour P. Majchrzak M. Villalobos A. White WF. J. Med. Chem.  2004,  47:  1575 
    CrossrefSuche in Google Scholar
  • 3a Perrier V. Wallace AC. Kaneko K. Safar J. Prusiner SB. Cohen FE. Proc. Natl. Acad. Sci. U.S.A.  2000,  97:  6073 
    Suche in Google Scholar
  • 3b Trankle WG. Kopach ME. Org. Process Res. Dev.  2007,  11:  913 
    Suche in Google Scholar
  • 4a Herradura PS. Pendola KA. Guy RK. Org. Lett.  2000,  2:  2019 
    Suche in Google Scholar
  • 4b Kwong FY. Buchwald SL. Org. Lett.  2002,  4:  3517 
    Suche in Google Scholar
  • 4c Li GY. Zheng G. Noonan AF. J. Org. Chem.  2001,  66:  8677 
    Suche in Google Scholar
  • 4d Hickman RJS. Christie BJ. Guy RW. White TJ. Aust. J. Chem.  1985,  38:  899 
    Suche in Google Scholar
  • 4e Taniguchi N. Onami T. J. Org. Chem.  2004,  69:  915 
    Suche in Google Scholar
  • 4f Adapa RS. Alam MM. Ramu RE. Chem. Lett.  2004,  33:  1614 
    Suche in Google Scholar
  • 5a Cheng Y. Tetrahedron  2002,  58:  4931 
    Suche in Google Scholar
  • 5b McDonald JW. Le Bleu RE. Quin LD. Bradsher CK. J. Org. Chem.  1961,  26:  4944 
    Suche in Google Scholar
  • 5c Tundo P. Anastas P. Black DS. Breen J. Collins T. Memoli S. Miyamoto J. Polyakoff M. Tumas W. Pure Appl. Chem.  2000,  72:  1207 
    Suche in Google Scholar
  • 6a Breslow R. Rideout DC. J. Am. Chem. Soc.  1980,  102:  7816 
    Suche in Google Scholar
  • 6b Narayan S. Muldoon J. Finn MG. Fokin FV. Kolb HC. Sharpless KB. Angew. Chem. Int. Ed.  2005,  44:  3275 
    Suche in Google Scholar
  • 6c Shapiro N. Vigalok A. Angew. Chem. Int. Ed.  2008,  47:  2849 
    Suche in Google Scholar
  • 6d Khatik GL. Kumar R. Chakraborti AK. Org. Lett.  2006,  8:  2433 
    Suche in Google Scholar
  • 6e Wang Z. Cui YT. Xu ZB. Qu J. J. Org. Chem.  2008,  73:  2270 
    Suche in Google Scholar
  • 6f Azizi N. Saisi MR. Org. Lett.  2005,  7:  3649 
    Suche in Google Scholar
  • 7a Sreedhar B. Reddy PS. Krishna CSV. Babu PV. Tetrahedron Lett.  2007,  48:  7882 
    Suche in Google Scholar
  • 7b Sreedhar B. Reddy PS. Kumar NS. Tetrahedron Lett.  2006,  47:  3055 
    Suche in Google Scholar
  • 7c Sreedhar B. Reddy PS. Prakash BV. Ravindra A. Tetrahedron Lett.  2005,  46:  7019 
    Suche in Google Scholar
  • 9a Akerlof GC. Oshry HI. J. Am. Chem. Soc.  1950,  72:  2844 
    Suche in Google Scholar
  • 9b Miller DJ. Hawthorne SB. J. Chem. Eng. Data  2000,  45:  78 
    Suche in Google Scholar
  • 10 van der Plas HC. Acc. Chem. Res.  1978,  11:  462 
    CrossrefSuche in Google Scholar
8

Elkington J.; http://www.sustainability.co.uk/sustainability.htm>.