PDF herunterladen
Synthesis 2012(3): 380-388  
DOI: 10.1055/s-0031-1290067
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Stereoselective Synthesis of (Z)-1,2-Dithio-1-alkenes via Copper-Catalyzed Thiolation of (Z)-2-Bromovinyl Sulfides

Hui Xua, Wanzhi Chen*a, Jiuxi Chenb, Huayue Wu*b
a Department of Chemistry, Zhejiang University, Xixi Campus, Hangzhou 310028, P. R. of China
Fax: +86(571)88273314; e-Mail: chenwzz@zju.edu.cn;
b College of Chemistry & Material Engineering, Wenzhou University, Wenzhou 325035, P. R. of China
e-Mail: hywu3@163.com;
Weitere Informationen

Publikationsverlauf

Received 31 October 2011
Publikationsdatum:
03. Januar 2012 (online)

    Lizenzen und Reprints Alle Artikel dieser Rubrik

Abstract

We describe a new method for the stereoselective synthesis of (Z)-1,2-dithio-1-alkenes via copper-catalyzed cross-coupling of (Z)-2-bromovinyl sulfides and thiols. The desired products are obtained in good to excellent yields. The double bond geometry of the starting (Z)-2-bromovinyl sulfides is retained under these reaction conditions.

Key words

copper catalyst - cross-coupling - thiolation - (Z)-2-bromovinyl sulfide - (Z)-1,2-dithio-1-alkene

    References

  • 1 Beletskaya IP. Ananikov VP. Chem. Rev.  2011,  111:  1596 
    Google Scholar
  • 2 Kondo T. Mitsudo T. Chem. Rev.  2000,  100:  3205 
    Google Scholar
  • 3 Lauterbach C. Fabian J. Eur. J. Inorg. Chem.  1999,  1995 
    Google Scholar
  • 4 Clemenson PI. Coord. Chem. Rev.  1990,  106:  171 
    Google Scholar
  • 5 Ananikov VP. Gayduk KA. Beletskaya IP. Khrustalev VN. Antipin MY. Chem. Eur. J.  2008,  14:  2420 
    Google Scholar
  • 6 Ananikov VP. Kabeshov MA. Beletskaya IP. Synlett  2005,  1015 
    Google Scholar
  • 7 Ananikov VP. Kabeshov MA. Beletskaya IP. Aleksandrov GG. Eremenko IL. J. Organomet. Chem.  2003,  687:  451 
    Google Scholar
  • 8 Ananikov VP. Kabeshov MA. Beletskaya IP. Khrustalev VN. Antipin MY. Organometallics  2005,  24:  1275 
    Google Scholar
  • 9 Arisawa M. Yamaguchi M. Org. Lett.  2001,  3:  763 
    Google Scholar
  • 10 Benati L. Montevecchi PC. Spagnolo P. J. Chem. Soc., Perkin Trans. 1  1992,  1659 
    Google Scholar
  • 11 Cai MZ. Wang YG. Hao WY. Green Chem.  2007,  9:  1180 
    Google Scholar
  • 12 Fujie S. Matsumoto K. Suga S. Nokami T. Yoshida J. Tetrahedron  2010,  66:  2823 
    Google Scholar
  • 13 Heiba EI. Dessau RM. J. Org. Chem.  1967,  32:  3837 
    Google Scholar
  • 14 Kuniyasu H. Ogawa A. Miyazaki SI. Ryu I. Kambe N. Sonoda N. J. Am. Chem. Soc.  1991,  113:  9796 
    Google Scholar
  • 15 Manarin F. Roehrs JA. Prigol M. Alves D. Nogueira CW. Zeni G. Tetrahedron Lett.  2007,  48:  4805 
    Google Scholar
  • 16 Usugi S. Yorimitsu H. Shinokubo H. Oshima K. Org. Lett.  2004,  6:  601 
    Google Scholar
  • 17 Zou KB. Yin XH. Liu WQ. Qiu RH. Li RX. Shao LL. Li YH. Xu XH. Yang RH. Synth. Commun.  2009,  39:  2464 
    Google Scholar
  • 18 Tan P. Yin XH. Yu AH. Qiu RH. Peng LF. Xu XH. Zhao YL. Tang RR. Chin. J. Chem.  2011,  29:  765 
    Google Scholar
  • 19 Sperotto E. van Klink GPM. de Vries JG. van Koten G. J. Org. Chem.  2008,  73:  5625 
    Google Scholar
  • 20 Jammi S. Sakthivel S. Rout L. Mukherjee T. Mandal S. Mitra R. Saha P. Punniyamurthy T. J. Org. Chem.  2009,  74:  1971 
    Google Scholar
  • 21 Rout L. Sen TK. Punniyamurthy T. Angew. Chem. Int. Ed.  2007,  46:  5583 
    Google Scholar
  • 22 Chen YJ. Chen HH. Org. Lett.  2006,  8:  5609 
    Google Scholar
  • 23 Bates CG. Gujadhur RK. Venkataraman D. Org. Lett.  2002,  4:  2803 
    Google Scholar
  • 24 Lv X. Bao WL. J. Org. Chem.  2007,  72:  3863 
    Google Scholar
  • 25 You W. Yan XY. Liao QA. Xi CJ. Org. Lett.  2010,  12:  3930 
    Google Scholar
  • 26 Zhao QW. Li L. Fang YW. Sun DQ. Li CZ. J. Org. Chem.  2009,  74:  459 
    Google Scholar
  • 27 Kabir MH. Van Linn ML. Monte A. Cook JM. Org. Lett.  2008,  10:  3363 
    Google Scholar
  • 28 Bates CG. Saejueng P. Doherty MQ. Venkataraman D. Org. Lett.  2004,  6:  5005 
    Google Scholar
  • 29 Kabir MS. Lorenz M. Van Linn ML. Namjoshi OA. Ara S. Cook JM. J. Org. Chem.  2010,  75:  3626 
    Google Scholar
  • 30 Zheng YF. Du XF. Bao WL. Tetrahedron Lett.  2006,  47:  1217 
    Google Scholar
  • 31 Liu Y. Bao W. Tetrahedron Lett.  2007,  48:  4785 
    Google Scholar
  • 32 Kao H.-L. Lee C.-F. Org. Lett.  2011,  13:  5204 
    Google Scholar
  • 33 Xu H. Gu SJ. Chen WZ. Li DC. Dou JM. J. Org. Chem.  2011,  76:  2448 
    Google Scholar
  • 34 Xu H. Zhang Y. Huang JQ. Chen WZ. Org. Lett.  2010,  12:  3704 
    Google Scholar
  • 35 Kondoh A. Yorimitsu H. Oshima K. Org. Lett.  2007,  9:  1383 
    Google Scholar
  • 36 Kuniyasu H. Ohtaka A. Nakazono T. Kinomoto M. Kurosawa H. J. Am. Chem. Soc.  2000,  122:  2375 
    Google Scholar