Download PDF
Synthesis 2011(16): 2561-2566  
DOI: 10.1055/s-0030-1260077
SPECIALTOPIC
© Georg Thieme Verlag Stuttgart ˙ New York

Cobalt-Catalyzed Alkenylation of Thiazoles with Alkynes via C-H Bond Functionalization

Zhenhua Ding, Naohiko Yoshikai*
Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore 637371, Singapore
Fax: +65(6791)1961; e-Mail: nyoshikai@ntu.edu.sg;
Further Information

Publication History

Received 15 March 2011
Publication Date:
17 June 2011 (online)

    Permissions and Reprints All articles of this category

Abstract

A cobalt-Xantphos catalyst has been developed for the syn addition of (benzo)thiazoles to internal alkynes via C-H bond functionalization. The reaction affords C2-alkenylated (benzo)thiazoles with high regio- and stereoselectivities under mild conditions.

Key words

cobalt - C-H activation - heterocycles - hydroarylation - alkynes

    References

  • For recent reviews, see:
  • 1a Hirano K. Miura M. Synlett  2011,  294 
    Google Scholar
  • 1b Colby DA. Bergman RG. Ellman JA. Chem. Rev.  2010,  110:  624 
    Google Scholar
  • 1c Lyons TW. Sanford MS. Chem. Rev.  2010,  110:  1147 
    Google Scholar
  • 1d Sun CL. Li BJ. Shi ZJ. Chem. Commun.  2010,  46:  677 
    Google Scholar
  • 1e Ackermann L. Chem. Commun.  2010,  46:  4866 
    Google Scholar
  • 1f Chen X. Engle KM. Wang DH. Yu JQ. Angew. Chem. Int. Ed.  2009,  48:  5094 
    Google Scholar
  • 1g Ackermann L. Vicente R. Kapdi AR. Angew. Chem. Int. Ed.  2009,  48:  9792 
    Google Scholar
  • 1h Daugulis O. Do HQ. Shabashov D. Acc. Chem. Res.  2009,  42:  1074 
    Google Scholar
  • 1i Kakiuchi F. Kochi T. Synthesis  2008,  3013 
    Google Scholar
  • 2 Ding ZH. Yoshikai N. Org. Lett.  2010,  12:  4180 
    CrossrefPubMedGoogle Scholar
  • Related reaction with Ni catalyst:
  • 3a Nakao Y. Kanyiva KS. Oda S. Hiyama T. J. Am. Chem. Soc.  2006,  128:  8146 
    Google Scholar
  • 3b Kanyiva KS. Nakao Y. Hiyama T. Heterocycles  2007,  72:  677 
    Google Scholar
  • 3c Mukai T. Hirano K. Satoh T. Miura M. J. Org. Chem.  2009,  74:  6410 
    Google Scholar
  • 3d Nakao Y. Kashihara N. Kanyiva KS. Hiyama T. Angew. Chem. Int. Ed.  2010,  49:  4451 
    Google Scholar
  • Related reaction with Rh catalyst:
  • 4a Tan KL. Bergman RG. Ellman JA. J. Am. Chem. Soc.  2002,  124:  13964 
    Google Scholar
  • 4b Tan KL. Park S. Ellman JA. Bergman RG.
    J. Org. Chem.  2004,  69:  7329 
    Google Scholar
  • 5a Cahiez G. Moyeux A. Chem. Rev.  2010,  110:  1435 
    Google Scholar
  • 5b Hess W. Treutwein J. Hilt G. Synthesis  2008,  3537 
    Google Scholar
  • 5c Yorimitsu H. Oshima K. Pure Appl. Chem.  2006,  78:  441 
    Google Scholar
  • For leading references on direct C2-functionalization of thiazoles, see:
  • 7a Do HQ. Daugulis O. J. Am. Chem. Soc.  2007,  129:  12404 
    Google Scholar
  • 7b Lewis JC. Berman AM. Bergman RG. Ellman JA. J. Am. Chem. Soc.  2008,  130:  2493 
    Google Scholar
  • 7c Besselievre F. Piguel S. Angew. Chem. Int. Ed.  2009,  48:  9553 
    Google Scholar
  • 7d Canivet J. Yamaguchi J. Ban I. Itami K. Org. Lett.  2009,  11:  1733 
    Google Scholar
  • 7e Hachiya H. Hirano K. Satoh T. Miura M. Org. Lett.  2009,  11:  1737 
    Google Scholar
  • 7f Matsuyama N. Hirano K. Satoh T. Miura M. Org. Lett.  2009,  11:  4156 
    Google Scholar
  • 7g Boogaerts IIF. Nolan SP.
    J. Am. Chem. Soc.  2010,  132:  8858 
    Google Scholar
  • 7h Do HQ. Daugulis O. Org. Lett.  2010,  12:  2517 
    Google Scholar
  • 7i Huang JK. Chan J. Chen Y. Borths CJ. Baucom KD. Larsen RD. Faul MM. J. Am. Chem. Soc.  2010,  132:  3674 
    Google Scholar
  • 7j Matsuyama N. Kitahara M. Hirano K. Satoh T. Miura M. Org. Lett.  2010,  12:  2358 
    Google Scholar
  • 7k Mukai T. Hirano K. Satoh T. Miura M. Org. Lett.  2010,  12:  1360 
    Google Scholar
  • 7l Truong T. Alvarado J. Tran LD. Daugulis O. Org. Lett.  2010,  12:  1200 
    Google Scholar
  • 7m Xie K. Yang ZY. Zhou XJ. Li XJ. Wang SZ. Tan Z. An XY. Guo CC. Org. Lett.  2010,  12:  1564 
    Google Scholar
  • 8 Yoshikai N. Synlett  2011,  1047 
    Article in Thieme ConnectGoogle Scholar
  • 9a Gao K. Lee PS. Fujita T. Yoshikai N. J. Am. Chem. Soc.  2010,  132:  12249 
    Google Scholar
  • 9b Gao K. Yoshikai N. J. Am. Chem. Soc.  2011,  133:  400 
    Google Scholar
  • 9c Gao K. Yoshikai N. Angew. Chem. Int. Ed.  2011,  DOI: 10.1002/anie.201101823 
    Google Scholar
  • 10a Chen Q. Ilies L. Nakamura E. J. Am. Chem. Soc.  2011,  133:  428 
    Google Scholar
  • 10b Li B. Wu Z.-H. Gu Y.-F. Sun C.-L. Wang B.-Q. Shi Z.-J. Angew. Chem. Int. Ed.  2011,  50:  1109 
    Google Scholar
  • 10c Kim JY. Cho SH. Joseph J. Chang S. Angew. Chem. Int. Ed.  2010,  49:  9899 
    Google Scholar
  • 10d Truong T. Alvardo J. Tran LD. Daugulis O. Org. Lett.  2010,  12:  1200 
    Google Scholar
  • 10e Ilies L. Chen Q. Zeng X. Nakamura E. J. Am. Chem. Soc.  2011,  133:  5221 
    Google Scholar
  • 11a Roger J. Pozgan F. Doucet H. J. Org. Chem.  2009,  74:  1179 
    Google Scholar
  • 11b Liegault B. Lapointe D. Caron L. Vlassova A. Fagnou K. J. Org. Chem.  2009,  74:  1826 
    Google Scholar
  • 11c Parisien M. Valette D. Fagnou K. J. Org. Chem.  2005,  70:  7578 
    Google Scholar
  • 11d Pivsa-Art S. Satoh T. Kawamura Y. Miura M. Nomura M. Bull. Chem. Soc. Jpn.  1998,  71:  467 
    Google Scholar
  • 12 Zhao HY. Foss FW. Breslow R. J. Am. Chem. Soc.  2008,  130:  12590 
    CrossrefGoogle Scholar
6

A small part of the present work was communicated in ref 2.