RSS-Feed abonnieren
Bitte kopieren Sie die angezeigte URL und fügen sie dann in Ihren RSS-Reader ein.
https://www.thieme-connect.de/rss/thieme/de/10.1055-s-00000084.xml
Synthesis 2012; 44(10): 1507-1510
DOI: 10.1055/s-0031-1290813
DOI: 10.1055/s-0031-1290813
special topic
Microwave-Assisted Copper-Catalyzed Cross-Coupling Reaction of Alkynes with Aryl Iodides and Vinyl Halides
Weitere Informationen
Publikationsverlauf
Received: 20. Februar 2012
Accepted: 05. März 2012
Publikationsdatum:
02. April 2012 (online)
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
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis.
- Supporting Information
-
References
- 1a Nicolaou KC, Smith AL In Modern Acetylene Chemistry . Stang PJ, Diederich F. VCH; Weinheim: 1995
- 1b Sonogashira K In Handbook of Organopalladium Chemistry for Organic Synthesis . Negishi E. Wiley; New York: 2002. 493-529
- 1c Negishi E, Xu C In Handbook of Organopalladium Chemistry for Organic Synthesis . Negishi E. Wiley; New York: 2002. 531-549
- 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
- 5a Kappe CO, Dallinger D, Murphree SS In Practical Microwave Synthesis for Organic Chemists: Strategies, Instruments, and Protocols. Wiley-VCH; Weinheim: 2009
- 5b Topics in Current Chemistry: Microwave Methods in Organic Synthesis . Vol. 266. Larhed M, Olafsson K. Springer; Berlin/Heidelberg: 2006
- 5c Microwaves in Organic Synthesis . 2nd ed.; Loupy A. Wiley-VCH; Weinheim: 2006
-
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