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Synthesis 2009(5): 829-835
DOI: 10.1055/s-0028-1083375
DOI: 10.1055/s-0028-1083375
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New York
Sonogashira Cross-Coupling Reactions and Construction of the Indole Ring System Using a Robust, Silica-Supported Palladium Catalyst
Weitere Informationen
Received
26 September 2008
Publikationsdatum:
11. Februar 2009 (online)
Publikationsverlauf
Publikationsdatum:
11. Februar 2009 (online)
Abstract
The use of a recyclable silica-supported palladium catalyst in Sonogashira couplings and indole syntheses using a range of functionalised substrates is described. The catalyst is shown to be both robust and versatile, effecting the synthesis of 2-phenylindole in quantitative yield without the need for N-protection, a copper cocatalyst, a base, or a solvent.
Key words
Sonogashira cross-coupling - silica-supported catalysis - palladium catalyst - indoles - enynes
- 1
Sommer W.Weck M. Coord. Chem. Rev. 2007, 251: 860 - 2
Gonthier E.Breinbauer R. Synlett 2003, 1049 - 3
Tyrrell E.Al-Saardi A.Millet J. Synlett 2005, 487 - 4
Polshettiwar V.Hesemann P.Moreau J. Tetrahedron 2007, 63: 6784 - 5
Polshettiwar V.Varma R. Tetrahedron 2008, 64: 4637 - 6
Bandini M.Luque R.Budarin V.Macquarrie D. Tetrahedron 2005, 61: 9860 - 7
Gotov B.Toma S.Macquarrie D. New J. Chem. 2000, 24: 597 - 8
Kim J.-H.Lee D.-H.Jun B.-H.Lee Y.-S. Tetrahedron Lett. 2007, 48: 7079 - 9
Cai M.Xu Q.Sha J. J. Mol. Catal. A: Chem. 2007, 272: 293 - 10
Cai M.Sha J.Xu Q. Tetrahedron 2007, 63: 4642 - 11
Gruber M.Chouzier S.Koehler K.Djakovitch L. Appl. Catal., A 2004, 265: 161 - 12
Chouzier S.Gruber M.Djakovitch L. J. Mol. Catal. A: Chem. 2004, 212: 43 - 13
Hiroya K.Itoh S.Sakamoto T. Tetrahedron 2005, 61: 10958 - 14
Palimkar S.Kumar H.Lahoti R.Srinivasan K. Tetrahedron 2006, 62: 5109 - 15
Wang Z.Wu J. Tetrahedron 2008, 64: 1736 - 16
Glaser C. Ber. Dtsch. Chem. Ges. 1869, 2: 422 - 18
Hiroya K.Itoh S.Ozawa M.Kanamori Y.Sakamoto T. Tetrahedron Lett. 2002, 43: 1277 - 19
Siriwardana A.Kamada M.Itaru N.Yamamoto Y. J. Org. Chem. 2005, 70: 5932 - 20
Amatore C.Anny J.Laure M.Louis R. J. Organomet. Chem. 2007, 692: 1457 - 21
Sole D.Vallverdu L.Solans X.Font-Bardia M. Chem. Commun. 2005, 2738 - 22
Li P.Wang L.Li H. Tetrahedron 2005, 61: 8633 - 23
Yang F.Cui X.Li Y.Zhang J.Reg G.Wu Y. Tetrahedron 2007, 63: 1963 - 24
Feurerstein M.Doucet H.Santelli M. J. Mol. Catal. A: Chem. 2006, 256: 75 - 25
Kabalka G.Wang L.Pagni R. Tetrahedron 2001, 57: 8017 - 26
Kollhofer A.Plenio H. Adv. Synth. Catal. 2005, 347: 1295 - 27
Kamikawa T.Hiyashi T. J. Org. Chem. 1998, 63: 8922 - 28
Fleckenstein C.Plenio H. Green Chem. 2008, 10: 563 - 29
Koradin C.Dohle W.Rodriguez A.Schmid B.Knochel P. Tetrahedron 2003, 59: 1571 - 30
Novak I.Wang L.Huang H.Huang W. Tetrahedron 1997, 39: 13339 - 31
Ueno M.Hori C.Suzawa K.Ebisawa M.Kondo Y. Eur. J. Org. Chem. 2005, 10: 1965 - 32
Pornet J.Princet B.Mbaze Mevaa L.Miginiac L. Synth. Commun. 1996, 26: 2099 - 33
Hudkins R.Diebold J.Marsh F. J. Org. Chem. 1995, 60: 6218 - 34
Cacchi S.Carnicelli V.Marinelli F. J. Organomet. Chem. 1994, 475: 289
References
Sigma-Aldrich ref. P26600, CAS no. 948-65-2.