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Synthesis 2009(16): 2785-2789
DOI: 10.1055/s-0029-1216876
DOI: 10.1055/s-0029-1216876
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New YorkCopper(I)-Catalyzed Caryl-Calkynyl Bond Formation of Aryl Iodides with Terminal Alkynes
Further Information
Received
6 April 2009
Publication Date:
26 June 2009 (online)
Publication History
Publication Date:
26 June 2009 (online)

Abstract
A wide range of internal alkynes are synthesized from the corresponding aryl iodides and terminal alkynes by Sonogashira-type cross-coupling reactions through Caryl-Calkynyl bond formation in the presence of a catalytic amount of readily available DBU-CuBr complex under mild reaction conditions.
Key words
copper catalyst - coupling reaction - arylated alkynes - C-C bond formation - Sonogashira coupling - nitrogen ligands
- 1a
Sonogashira K.Tohda Y.Hagihara N. Tetrahedron Lett. 1975, 16: 4467 - 1b
Sonogashira K. In Comprehensive Organic Synthesis Vol. 3:Trost BM.Fleming I. Pergamon Press; Oxford: 1999. p.521 - 1c
Kawanami H.Matsushima K.Sato M.Ikushima Y. Angew. Chem. Int. Ed. 2007, 46: 5129 - 1d
Yi WB.Chi C.Wang X. Eur. J. Org. Chem. 2007, 3445 - 1e
Li JH.Liang Y.Xie YX. J. Org. Chem. 2005, 70: 4393 - 2
Theil F. Angew. Chem. Int. Ed. 1999, 38: 2345 - 3
Stephens RD.Castro CE. J. Org. Chem. 1963, 28: 3313 - 4a
Okuro K.Furuune M.Miura M.Nomura M. Tetrahedron Lett. 1992, 33: 5363 - 4b
Okuro K.Furuune M.Enna M.Miura M.Nomura M. J. Org. Chem. 1993, 58: 4716 - 4c
Saejueng P.Bates CG.Venkataraman D. Synthesis 2005, 1706 - 4d
Tang BX.Wang F.Li JH.Xie YX.Zhang MB. J. Org. Chem. 2007, 72: 6294 - 4e
Gujadhar RK.Bates CG.Venkataraman D. Org. Lett. 2001, 3: 4315 - 4f
Ma D.Liu F. Chem. Commun. 2004, 1934 - 4g
He H.Wu YJ. Tetrahedron Lett. 2004, 45: 3237 - 4h
Colacino E.Daich L.Martinez J.Lamaty F. Synlett 2007, 1279 - 4i
Chinchilla R.Nájera C. Chem. Rev. 2007, 107: 874 - 4j
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 - 4k
Monnier F.Turtaut F.Doroure L.Taillefer M. Org. Lett. 2008, 10: 3203 - 4l
Guan JT.Yu G.-A.Chen L.Weng TQ.Yuan JJ.Liu SH. Appl. Organomet. Chem. 2009, 23: 75 - 5a
Mannam S.Kumar SA.Sekar G. Adv. Synth. Catal. 2007, 349: 2253 - 5b
Mannam S.Sekar G. Tetrahedron Lett. 2008, 49: 1083 - 5c
Mannam S.Sekar G. Tetrahedron Lett. 2008, 49: 2457 - 5d
Alamsetti SK.Sreedevi M.Muthupandi P.Sekar G. Chem. Eur. J. 2009, 15: 1086 - 6a
Naidu AB.Raghunath OR.Prasad DJC.Sekar G. Tetrahedron Lett. 2008, 49: 1057 - 6b
Naidu AB.Sekar G. Tetrahedron Lett. 2008, 49: 3147 - 6c
Prasad DJC.Naidu AB.Sekar G. Tetrahedron Lett. 2009, 50: 1411 - 7
Mino T.Shirae Y.Saito T.Sakamoto M.Fujita T. J. Org. Chem. 2006, 71: 9499 - 8
Okuro K.Furuune M.Enna M.Miura M.Nomura M. J. Org. Chem. 1993, 58: 4716 - 9
Arcadi A.Cacchi S.Marinelli F.Pace P.Sanzi G. Synlett 1995, 823 - 10
Jincan Y.Zhiyuan W.Lei W. J. Chem. Res. 2004, 71 - 11
Tang BX.Wang F.Li JH.Xie YX.Zhang MB. J. Org. Chem. 2007, 72: 6294 - 12
Soler R.Cacchi S.Fabrizi G.Forte G.Martin L.Martinez S.Molins E.Manas MM.Petrucci F.Roig A.Sebastian RR.Vallribera A. Synthesis 2007, 3068 - 13
Moon J.Jeong M.Nam H.Ju J.Moon JH.Jung HM.Lee S. Org. Lett. 2008, 10: 945 - 14
Liang Y.Xie YX.Li JH. J. Org. Chem. 2006, 71: 379 - 15
Urgaonkar S.Verkade JG. J. Org. Chem. 2004, 69: 5752