Download PDF
Synthesis 2011(17): 2789-2795  
DOI: 10.1055/s-0030-1260126
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Efficient Palladium-Catalyzed Suzuki-Miyaura Cross-Coupling of Iodoethynes with Arylboronic Acids under Aerobic Conditions

Jian-Sheng Tang*a,b, Ye-Xiang Xieb, Zhi-Qiang Wangc, Jin-Heng Li*b
a Mathematics and Science Department, Hunan First Normal University, Changsha 410205, P. R. of China
b State Key Laboratory of Chemo/Biosensing and Chemometrics, College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082, P. R. of China
Fax: +86(731)88872531; e-Mail: jhli@hunnu.edu.cn; e-Mail: hnyztjs@163.com;
c Key Laboratory of Chemical Biology & Traditional Chinese Medicine Research (Ministry of Education), Hunan Normal University, Changsha 410081, P. R. of China
Further Information

Publication History

Received 28 April 2011
Publication Date:
18 July 2011 (online)

    Permissions and Reprints All articles of this category

Abstract

Ligand-free palladium-catalyzed Suzuki-Miyaura cross-coupling of iodoethynes with arylboronic acids under aerobic conditions has been developed. In the presence of palladium(II) acetate and cesium carbonate, a variety of iodoethynes underwent the Suzuki­-Miyaura cross-coupling reaction with arylboronic acids at room temperature to afford the corresponding internal alkynes in moderate to good yields. It is noteworthy that this protocol proceeds under mild and aerobic conditions without the aid of ligands.

Key words

palladium - iodoethynes - arylboronic acids - Suzuki-Miyaura - cross-coupling - alkynes

    References

  • 1a Tang S. Peng P. Pi S.-F. Liang Y. Wang N.-X. Li J.-H. Org. Lett.  2008,  10:  1179 
    Google Scholar
  • 1b Tang S. Peng P. Wang Z.-Q. Tang B.-X. Deng C.-L. Li J.-H. Zhong P. Wang N.-X. Org. Lett.  2008,  10:  1875 
    Google Scholar
  • 1c Tang S. Peng P. Zhong P. Li J.-H. J. Org. Chem.  2008,  73:  5476 
    Google Scholar
  • 1d Peng P. Tang B.-X. Pi S.-F. Liang Y. Li J.-H.
    J. Org. Chem.  2009,  74:  3569 
    Google Scholar
  • 1e Tang D.-J. Tang B.-X. Li J.-H. J. Org. Chem.  2009,  74:  6749 
    Google Scholar
  • 1f Jiang T.-S. Tang R.-Y. Zhang X.-G. Li X.-H. Li J.-H. J. Org. Chem.  2009,  74:  8834 
    Google Scholar
  • 2a Pinto A. Neuville L. Retailleau P. Zhu J. Org. Lett.  2006,  8:  4927 
    Google Scholar
  • 2b Pinto A. Neuville L. Zhu J. Angew. Chem. Int. Ed.  2007,  46:  3291 
    Google Scholar
  • 3a Cheung WS. Patch RJ. Player MR. J. Org. Chem.  2005,  70:  3741 
    Google Scholar
  • 3b Yanada R. Obika S. Inokuma T. Yanada K. Yamashita M. Ohta S. Takemoto Y. J. Org. Chem.  2005,  70:  6972 
    Google Scholar
  • 3c Couty S. Liégault B. Meyer C. Cossy J. Org. Lett.  2004,  6:  2511 
    Google Scholar
  • 3d D’Souza DM. Rominger F. Müller TJJ. Angew. Chem. Int. Ed.  2005,  44:  153 
    Google Scholar
  • 3e Yanada R. Obika S. Oyama M. Takemoto Y. Org. Lett.  2004,  6:  2825 
    Google Scholar
  • 3f Kamijo S. Sasaki Y. Kanazawa C. Schüsseler T. Yamamoto Y. Angew. Chem. Int. Ed.  2005,  44:  7718 
    Google Scholar
  • 3g Shintani R. Yamagami T. Hayashi T. Org. Lett.  2006,  8:  4799 
    Google Scholar
  • 4a Diek HA. Heck FR. J. Organomet. Chem.  1975,  93:  259 
    Google Scholar
  • 4b Cassar L. J. Organomet. Chem.  1975,  93:  253 
    Google Scholar
  • 4c Sonogashira K. Tohda Y. Hagihara N. Tetrahedron Lett.  1975,  4467 
    Google Scholar
  • 4d Chinchilla R. Nájera C. Chem. Rev.  2007,  107:  874 
    Google Scholar
  • For selected reviews, see:
  • 5a Metal-Catalyzed Cross-Coupling Reactions   Diederich F. Stang PJ. Wiley-VCH; Weinheim / Germany: 1998. 
    Google Scholar
  • 5b Cross-Coupling Reaction   Miyaura N. Springer; Berlin: 2002. 
    Google Scholar
  • 5c Metal-Catalyzed Cross-Coupling Reactions   2nd ed.:  Diederich F. de Meijere A. Wiley-VCH; Weinheim: 2004. 
    Google Scholar
  • 5d Transition Metals for Organic Synthesis, Building Blocks and Fine Chemicals   2nd ed.:  Beller M. Bolm C. Wiley-VCH; Weinheim: 2004. 
    Google Scholar
  • 5e Xie Y.-X. Li J.-H. Yin D.-L. Chin. J. Org. Chem.  2006,  26:  1155 
    Google Scholar
  • 5f Handbook of Organopalladium Chemistry for Organic Synthesis   Negishi E. Wiley-Interscience; New York: 2002. 
    Google Scholar
  • 5g Shair MD. Yoon T. Danishefsky SJ. J. Org. Chem.  1994,  59:  3755 
    Google Scholar
  • 6a Zou G. Zhu J. Tang J. Tetrahedron Lett.  2003,  44:  8709 
    Google Scholar
  • 6b Yang F. Wu Y. Eur. J. Org. Chem.  2007,  3476 
    Google Scholar
  • 6c Pan C. Luo F. Wang W. Ye Z. Cheng J. Tetrahedron Lett.  2009,  50:  5044 
    Google Scholar
  • 6d Zhou M.-B. Wei W.-T. Xie Y.-X. Lei Y. Li J.-H. J. Org. Chem.  2010,  75:  5635 
    Google Scholar
  • 7 Wang Z.-Q. Tang B.-X. Zhang H.-P. Wang F. Li J.-H. Synthesis  2009,  891 
    Article in Thieme ConnectGoogle Scholar
  • 8 Butke GP. Felicita JM. Michalik J. Gorski RA. Rossi NF. Wemple J. J. Org. Chem.  1978,  43:  954 
    CrossrefGoogle Scholar
  • 9 Cheng J. Pan C.-D. Luo F. Wang W.-H. Ye Z.-S. Tetrahedron  2009,  50:  5044 
    CrossrefGoogle Scholar
  • 10 Ding S. Shi Z. Jiao N. Org. Lett.  2010,  12:  1540 
    Google Scholar
  • 11 Pi S.-F. Tang B.-X. Li J.-H. Liu Y.-L. Liang Y. Org. Lett.  2009,  11:  2309 
    CrossrefGoogle Scholar
  • 12 Zou G. Zhu J. Tang J. Tetrahedron Lett.  2003,  44:  8709 
    CrossrefGoogle Scholar