Synthesis 2012; 44(10): 1507-1510
DOI: 10.1055/s-0031-1290813
special topic
© Georg Thieme Verlag Stuttgart · New York

Microwave-Assisted Copper-Catalyzed Cross-Coupling Reaction of Alkynes with Aryl Iodides and Vinyl Halides

Wen-Ting Tsai
Department of Chemistry, National Chung Hsing University, Taichung, Taiwan 402, ROC, Fax: +886(4)22862547   Email: cfalee@dragon.nchu.edu.tw
,
Yun-Yung Lin
Department of Chemistry, National Chung Hsing University, Taichung, Taiwan 402, ROC, Fax: +886(4)22862547   Email: cfalee@dragon.nchu.edu.tw
,
Yu-Jen Wang
Department of Chemistry, National Chung Hsing University, Taichung, Taiwan 402, ROC, Fax: +886(4)22862547   Email: cfalee@dragon.nchu.edu.tw
,
Chin-Fa Lee*
Department of Chemistry, National Chung Hsing University, Taichung, Taiwan 402, ROC, Fax: +886(4)22862547   Email: cfalee@dragon.nchu.edu.tw
› Author Affiliations
Further Information

Publication History

Received: 20 February 2012

Accepted: 05 March 2012

Publication Date:
02 April 2012 (eFirst)

Abstract

The microwave-assisted, copper-catalyzed coupling of terminal alkynes with aryl iodides and vinyl halides is reported. In general, the reactions are completed in 10–30 min using 2–5 mol% [CuI(xantphos)] as a catalyst to provide the corresponding alkynes and enynes in good to excellent yields. A broad spectrum of aryl iodides­, vinyl iodides, and bromides are coupled with aryl- and alkyl­ alkynes.

Supporting Information

 
  • References

    • 2a Zhou L, Ye F, Ma J, Zhang Y, Wang J. Angew. Chem. Int. Ed. 2011; 50: 3510
    • 2b Sakai N, Komatsu R, Uchida N, Ikeda R, Konakahara T. Org. Lett. 2010; 12: 1300
    • 2c Hatakeyama T, Yoshimoto Y, Gabriel T, Nakamura M. Org. Lett. 2008; 10: 5341
    • 2d Kang B, Kim D.-h, Do Y, Chang S. Org. Lett. 2003; 5: 3041
    • 2e Shi J.-c, Zeng X, Negishi E.-i. Org. Lett. 2003; 5: 1825
    • For reviews, see:

    • 3a Heravi MM, Sadjadi S. Tetrahedron 2009; 65: 7761
    • 3b Chinchilla R, Nájera C. Chem. Rev. 2007; 107: 874
    • 3c Doucet H, Hierso J.-C. Angew. Chem. Int. Ed. 2007; 46: 834
    • 3d Nicolaou KC, Bulger PG, Sarlah D. Angew. Chem. Int. Ed. 2005; 44: 4442
    • 3e Negishi E, Anastasia L. Chem. Rev. 2003; 103: 1979
    • 3f Littke AF, Fu GC. Angew. Chem. Int. Ed. 2002; 41: 4176
    • 3g Siemsen P, Livingston RC, Diederich F. Angew. Chem. Int. Ed. 2000; 39: 2632
    • 3h Martin RE, Diederich F. Angew. Chem. Int. Ed. 1999; 38: 1350
    • 3i Grissom JW, Gunawardena GU, Klingberg D, Huang D. Tetrahedron 1996; 52: 6453
    • 3j Nicolaou KC, Dai W.-M. Angew. Chem. Int. Ed. 1991; 30: 1387
    • For selected examples, see:

    • 4a Lin C.-H, Wang Y.-J, Lee C.-F. Eur. J. Org. Chem. 2010; 4368
    • 4b Lin Y.-Y, Wang Y.-J, Cheng J.-H, Lee C.-F. Synlett 2012; 23: 930
    • 4c Monnier F, Turtaut F, Duroure L, Taillefer M. Org. Lett. 2008; 10: 3203
    • 4d Li J.-H, Li J.-L, Wang D.-P, Pi S.-F, Xie Y.-X, Zhang M.-B, Hu X.-C. J. Org. Chem. 2007; 72: 2053
    • 4e Xie Y.-X, Deng C.-L, Pi S.-F, Li J.-H, Yin D.-L. Chin. J. Chem. 2006; 24: 1290
    • 4f Saejueng P, Bates CG, Venkataraman D. Synthesis 2005; 1706
    • 4g Wang YF, Deng W, Liu L, Guo QX. Chin. Chem. Lett. 2005; 16: 1197
    • 4h Ma D, Liu F. Chem. Commun. 2004; 1934
    • 4i Gujadhur RK, Bates CG, Venkataraman D. Org. Lett. 2001; 3: 4315
    • 4j Okuro K, Furuune M, Enna M, Miura M, Nomura M. J. Org. Chem. 1993; 58: 4716
    • For recent reviews, see:

    • 6a Kappe CO. Chem. Soc. Rev. 2008; 37: 1127
    • 6b Coquerel Y, Rodriguez J. Eur. J. Org. Chem. 2008; 1125
    • 6c Dallinger D, Kappe CO. Chem. Rev. 2007; 107: 2563
    • 6d Larhed M, Moberg C, Hallberg A. Acc. Chem. Res. 2002; 35: 717
    • For selected examples on microwave-promoted systems using Pd/Cu catalyst, see:

    • 7a Erdélyi M, Gogoll A. J. Org. Chem. 2003; 68: 6431
    • 7b Erdélyi M, Gogoll A. J. Org. Chem. 2001; 66: 4165
    • 7c Chen Y, Markina N.-A, Larock R.-C. Tetrahedron 2009; 65: 8908
    • 7d Shook B.-C, Chakravarty D, Jackson P.-F. Tetrahedron Lett. 2009; 50: 1013
    • For examples on Pd-catalyzed systems by microwave heating, see:

    • 8a Sedelmeier J, Ley S.-V, Lange H, Baxendale I.-R. Eur. J. Org. Chem. 2009; 4412
    • 8b Awuah E, Capretta A. Org. Lett. 2009; 11: 3210
    • 8c Huang H, Liu H, Jiang H, Chen K. J. Org. Chem. 2008; 73: 6037
    • 9a He H, Wu Y.-J. Tetrahedron Lett. 2004; 45: 3237
    • 9b Wang J, Liu Z, Hu Y, Wei B, Kang L. Synth. Commun. 2002; 32: 1937
    • 10a Chen G, Xie J, Weng J, Zhu X, Zheng Z, Cai J, Wan Y. Synth. Commun. 2011; 41: 3123
    • 10b Chen G, Zhu X, Cai J, Wan Y. Synth. Commun. 2007; 37: 1355