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Synlett 2012(6): 930-934
DOI: 10.1055/s-0031-1290502
DOI: 10.1055/s-0031-1290502
LETTER
© Georg Thieme Verlag
Stuttgart ˙ New York
Copper-Catalyzed Coupling of Alkynes with Alkenyl Halides
Further Information
Received
1 December 2011
Publication Date:
15 March 2012 (online)
Publication History
Publication Date:
15 March 2012 (online)
Abstract
The synthesis of enynes from the coupling of terminal alkynes with alkenyl iodides and bromides is described. This system employs 1.0-5.0 mol% of CuI(Xantphos) as a catalyst. A variety of alkenyl iodides and bromides are coupled smoothly with terminal alkynes, affording enynes in good to excellent yields.
Key words
copper - cross-coupling - terminal alkyne - alkenyl halide - enyne
- Supporting Information for this article is available online:
- Supporting Information
- For reviews, see:
-
1a
Chinchilla R.Nájera C. Chem. Rev. 2007, 107: 874 -
1b
Doucet H.Hierso J.-C. Angew. Chem. Int. Ed. 2007, 46: 834 -
1c
Saito S.Yamamoto Y. Chem. Rev. 2000, 100: 2901 -
1d
Trost BM. Angew. Chem. Int. Ed. 1995, 34: 259 - 2
Nicolaou KC.Smith AL. In Modern Acetylene ChemistryStang PJ.Diederich F. VCH; Weinheim: 1995. - For examples, see:
-
3a
Bassetti M.Pasquini C.Raneri A.Rosato D. J. Org. Chem. 2007, 72: 4558 -
3b
Chen X.Xue P.Sung HHY.Williams ID.Peruzzini M.Bianchini C.Jia G. Organometallics 2005, 24: 4330 -
3c
Lee C.-C.Lin Y.-C.Liu Y.-H.Wang Y. Organometallics 2005, 24: 136 -
3d
Komeyama K.Kawabata T.Takehira K.Takaki K. J. Org. Chem. 2005, 70: 7260 -
3e
Katayama H.Yari H.Tanaka M.Ozawa F. Chem. Commun. 2005, 4336 -
3f
Ogoshi S.Ueta M.Oka M.Kurosawa H. Chem. Commun. 2004, 2732 -
3g
Katayama H.Nakayama M.Nakano T.Wada C.Akamatsu K.Ozawa F. Macromolecules 2004, 37: 13 -
3h
Nishiura M.Hou Z.Makatsuki Y.Yamaki T.Miyamoto T. J. Am. Chem. Soc. 2003, 125: 1184 -
3i
Yang C.Nolan SP. J. Org. Chem. 2002, 67: 591 -
3j
Rubina M.Gevorgyan V. J. Am. Chem. Soc. 2001, 123: 11107 -
3k
Trost BM.Sorum MT.Chan C.Harms AE.Rühter G. J. Am. Chem. Soc. 1997, 119: 698 -
3l
Trost BM.Chan C.Ruhter G. J. Am. Chem. Soc. 1987, 109: 3486 -
4a
Hoshi M.Nakayabu HH.Shirakawa K. Synthesis 2005, 1991 -
4b
Silveira CC.Braga AL.Vieira AS.Zeni G. J. Org. Chem. 2003, 68: 662 -
4c
Stang PJ.Kitamura T. J. Am. Chem. Soc. 1987, 109: 7561 -
5a
Sonogashira K. In Handbook of Organopalladium Chemistry for Organic SynthesisNegishi E. Wiley; New York: 2002. p.493-529 -
5b
Negishi E.Xu C. In Handbook of Organopalladium Chemistry for Organic SynthesisNegishi E. Wiley; New York: 2002. p.531-549 - For reviews, see:
-
6a
Heravi MM.Sadjadi S. Tetrahedron 2009, 65: 7761 -
6b
Chinchilla R.Nájera C. Chem. Rev. 2007, 107: 874 -
6c
Nicolaou KC.Bulger PG.Sarlah D. Angew. Chem. Int. Ed. 2005, 44: 4442 -
6d
Negishi E.Anastasia L. Chem. Rev. 2003, 103: 1979 -
6e
Littke AF.Fu GC. Angew. Chem. Int. Ed. 2002, 41: 4176 -
6f
Siemsen P.Livingston RC.Diederich F. Angew. Chem. Int. Ed. 2000, 39: 2632 -
6g
Martin RE.Diederich F. Angew. Chem. Int. Ed. 1999, 38: 1350 -
6h
Grissom JW.Gunawardena GU.Klingberg D.Huang D. Tetrahedron 1996, 52: 6453 -
6i
Nicolaou KC.Dai W.-M. Angew. Chem., Int. Ed. Engl. 1991, 30: 1387 - For selected examples, see:
-
7a
Lin C.-H.Wang Y.-J.Lee C.-F. Eur. J. Org. Chem. 2010, 4368 -
7b
Monnier F.Turtaut F.Duroure L.Taillefer M. Org. Lett. 2008, 10: 3203 -
7c
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 -
7d
Xie Y.-X.Deng C.-L.Pi S.-F.Li J.-H.Yin D.-L. Chin. J. Chem. 2006, 24: 1290 -
7e
Saejueng P.Bates CG.Venkataraman D. Synthesis 2005, 1706 -
7f
Wang YF.Deng W.Liu L.Guo QX. Chin. Chem. Lett. 2005, 16: 1197 -
7g
Ma D.Liu F. Chem. Commun. 2004, 1934 -
7h
Gujadhur RK.Bates CG.Venkataraman D. Org. Lett. 2001, 3: 4315 -
7i
Okuro K.Furuune M.Enna M.Miura M.Nomura M. J. Org. Chem. 1993, 58: 4716 -
8a
Liu Y.Yang J.Bao W. Eur. J. Org. Chem. 2009, 5317 -
8b
Xie X.Xu XB.Li HF.Xu XL.Yang JY.Li YZ. Adv. Synth. Catal. 2009, 351: 1263 -
8c
Wu M.Mao J.Guo J.Ji S. Eur. J. Org. Chem. 2008, 4050 -
8d
Bates CG.Saejueng P.Venkataraman D. Org. Lett. 2004, 6: 1441 -
8e
Okuro K.Furuune M.Enna M.Miura M.Nomura M. J. Org. Chem. 1993, 58: 4716 -
8f
Okuro K.Furuune M.Miura M.Nomura M. Tetrahedron Lett. 1992, 33: 5363 - Other methods for preparing enynes, see:
-
9a
Zhou L.Ye F.Ma J.Zhang Y.Wang J. Angew. Chem. Int. Ed. 2011, 50: 3510 -
9b
Sakai N.Komatsu R.Uchida N.Ikeda R.Konakahara T. Org. Lett. 2010, 12: 1300 -
9c
Hatakeyama T.Yoshimoto Y.Gabriel T.Nakamura M. Org. Lett. 2008, 10: 5341 -
9d
Kang B.Kim D.-h.Do Y.Chang S. Org. Lett. 2003, 5: 3041 -
9e
Shi J.-c.Zeng X.Negishi E.-i. Org. Lett. 2003, 5: 1825 - 10
Huang J.Chan J.Chen Y.Borths CJ.Baucom KD.Larsen RD.Faul MM. J. Am. Chem. Soc. 2010, 132: 3674