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Synthesis 2011(5): 816-820
DOI: 10.1055/s-0030-1258403
DOI: 10.1055/s-0030-1258403
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New York
Copper(II) Oxide Catalyzed Ligand-Free Coupling Reaction of Heteroarenes with Bromoalkynes [¹]
Further Information
Received
26 November 2010
Publication Date:
11 January 2011 (online)
Publication History
Publication Date:
11 January 2011 (online)
Abstract
The coupling reaction of imidazoles and pyrazoles with bromoacetylenes has efficiently been carried out under ligand-free conditions in the presence of copper(II) oxide as the catalyst using potassium hydroxide in 1,4-dioxane at 80 ˚C. The method is a simpler access to N-alk-1-ynyl- and/or N-(2-bromovinyl)-substituted heteroarenes.
Key words
coupling reaction - ligand-free conditions - copper(II) oxide - N-alkynylheteroarene - N-(2-bromovinyl)heteroarene
Part 217 in the series ‘Studies on novel synthetic methodologies’.
- 2
Ishihara T.Mantani T.Konno T.Yamanaka H. Tetrahedron 2006, 62: 3783 - 3
Joshi RV.Xu ZQ.Ksebati MB.Kessel D.Corbett TH.Drach JC.Zemlicka J. J. Chem. Soc., Perkin Trans. 1 1994, 1089 -
4a
Reisch J.Seeger U. Arch. Pharm. (Weinheim, Ger.) 1977, 310: 851 -
4b
Parsons CGR,Jirgensons A,Jaunzeme I,Kalvinsh I,Henrich M,Vanejevs M,Weil T,Kauss V,Danysz W, andJatzke C. inventors; WO 2007023290. - 5
Brabec C.Scharber M.Johansson H.Comoretto D.Dellepiane G.Moggio I.Cravino A.Hummelen JC.Sariciftci NS. Synth. Met. 1999, 101: 298 -
6a
Mulder JA.Kurtz KCM.Hsung RP. Synlett 2003, 1379 -
6b
Katritzky AR.Jiang R.Singh SK. Heterocycles 2004, 63: 1455 -
7a
Brandsma L.Mal’kina AG.Trofimov BA. Synth. Commun. 1994, 24: 2721 -
7b
Kitamura T.Tashi N.Tsuda K.Chen H.Fujiwara T. Heterocycles 2000, 52: 303 -
7c
Wei L.Mulder JA.Xiong H.Zificsak CA.Douglas CJ.Hsung RP. Tetrahedron 2001, 57: 459 -
8a
Laroche C.Li J.Freyer MW.Kerwin SM. J. Org. Chem. 2008, 73: 6462 -
8b
Burley GA.Davies DL.Griffith GA.Lee M.Sing K. J. Org. Chem. 2010, 75: 980 -
9a
Das B.Damodar K.Bhunia N. J. Org. Chem. 2009, 74: 5607 -
9b
Das B.Satyalakshmi G.Suneel K.Damodar K. J. Org. Chem. 2009, 74: 8400 -
9c
Das B.Reddy ChR.Kumar DN.Krishnaiah M.Narendar R. Synlett 2010, 391
References
Part 217 in the series ‘Studies on novel synthetic methodologies’.