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Synthesis 2014; 46(24): 3415-3422
DOI: 10.1055/s-0034-1379074
DOI: 10.1055/s-0034-1379074
paper
Pseudo Five-Component Synthesis of 3-(Hetero)arylmethyl-2,5-di(hetero)-aryl-Substituted Thiophenes via Sonogashira–Glaser Cyclization Sequence
Further Information
Publication History
Received: 04 July 2014
Accepted after revision: 13 August 2014
Publication Date:
17 September 2014 (online)
Abstract
The Sonogashira–Glaser sequence combined with a microwave-assisted cyclization is a powerful tool to synthesize unsymmetrically substituted conjugated thiophenes. A variety of 3-(hetero)arylmethyl-2,5-di(hetero)aryl-substituted thiophenes could be synthesized in moderate to excellent yields using a single Pd/Cu catalyst system. The presented method is strikingly simple to perform using commercially available starting materials. The obtained trisubstituted oligothiophene derivatives are interesting molecules for materials science.
Supporting Information
- for this article is available online at http://www.thieme-connect.com/products/ejournals/journal/ 10.1055/s-00000084.
- Supporting Information
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References
- 1a Mishra A, Ma C.-Q, Bäuerle P. Chem. Rev. 2009; 109: 1141
- 1b Padinger F, Rittberger RS, Sariciftci NS. Adv. Funct. Mater. 2003; 13: 85
- 2 Bey E, Marchais-Oberwinkler S, Werth R, Negri M, Al-Soud YA, Kruchten P, Oster A, Frotscher M, Birk B, Hartmann RW. J. Med. Chem. 2008; 51: 6725
- 3 Liu Y, Kumar A, Depauw S, David-Cordonnier M.-H, Lee MP, Ismail MA, Farahat AA, Say M, Chackal-Catoen S, Batista-Parra A, Neidle S, Boykin DW, Wilson WD. J. Am. Chem. Soc. 2011; 133: 10171
- 4 Minetto G, Raveglia LF, Sega A, Taddei M. Eur. J. Org. Chem. 2005; 5277
- 5 Heravi MM, Sadjadi S. Tetrahedron 2009; 65: 7761
- 6a Kotha S, Lahiri K, Kashinath D. Tetrahedron 2002; 58: 9633
- 6b Liégault B, Lapointe D, Caron L, Vlassova A, Fagnou K. J. Org. Chem. 2009; 74: 1826
- 7a Multicomponent Reactions 1 . Müller TJ. J. Georg Thieme Verlag; Stuttgart: 2013
- 7b Sunderhaus JD, Martin SF. Chem. Eur. J. 2009; 15: 1300
- 7c Isambert N, Lavilla R. Chem. Eur. J. 2008; 14: 8444
- 7d Orru RV. A, de Greef M. Synthesis 2003; 1471
- 7e Bonne D, Coquerel Y, Constantieux T, Rodriguez J. Tetrahedron: Asymmetry 2010; 21: 1085
- 8a Müller TJ. J, D’Souza DM. Pure Appl. Chem. 2008; 80: 609
- 8b Burke MD, Schreiber SL. Angew. Chem. Int. Ed. 2004; 43: 46
- 9a Müller TJ. J. Top. Organomet. Chem. 2006; 19: 149
- 9b D’Souza DM, Müller TJ. J. Chem. Soc. Rev. 2007; 36: 1095
- 9c Willy B, Müller TJ. J. Curr. Org. Chem. 2009; 13: 1777
- 9d Müller TJ. J. Top. Heterocycl. Chem. 2010; 25: 25
- 9e Müller TJ. J. Synthesis 2012; 44: 159
- 10 Merkul E, Urselmann D, Müller TJ. J. Eur. J. Org. Chem. 2011; 238
- 11 Urselmann D, Antovic D, Müller TJ. J. Beilstein J. Org. Chem. 2011; 7: 1499
- 12 Klukas F, Grunwald A, Menschel F, Müller TJ. J. Beilstein J. Org. Chem. 2014; 10: 672
- 13 Freeman F, Hengyao L, Qingbei Z. J. Org. Chem. 1994; 59: 4350
-
14a Yuan Y, Thomé I, Kim SH, Chen D, Beyer A, Bonnamour J, Zuidema E, Chang S, Bolm C. Adv. Synth. Catal. 2010; 352: 2892
- 14b Caubère P. Chem. Rev. 1993; 93: 2317
- 15 Brembilla A, Roizard D, Schoenleber J, Lochon P. Can. J. Chem. 1984; 62: 2330
- 16 Hofmann T, Schieberle P. J. Agric. Food Chem. 1995; 43: 2187
- 17 Houk J, Whitesides GM. J. Am. Chem. Soc. 1987; 109: 6825
- 18 Tal DM, Karlish SJ. D. Tetrahedron 1995; 51: 3823
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