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Synthesis 2019; 51(04): 859-864
DOI: 10.1055/s-0037-1611017
DOI: 10.1055/s-0037-1611017
paper
A Convenient Synthesis of Benzo[1,2-b:6,5-b′:3,4-c′′]trithiophenes Starting from Thiophene
This work was partially supported by NRF-2017R1D1A1B03031393. The authors declare no competing financial interest.Further Information
Publication History
Received: 21 August 2018
Accepted after revision: 17 September 2018
Publication Date:
10 October 2018 (online)
Abstract
A series of benzo[1,2-b:6,5-b′:3,4-c′′]trithiophenes were synthesized in four steps starting from thiophene. Thiophene was converted into 2,5-dialkylthiophenes upon dilithiation followed by treatment with various alkyl halides. The reaction of 2,5-dialkylthiophenes with Br2 easily afforded the corresponding 2,5-dialkyl-3,4-dibromothiophenes. Their coupling reactions with 3-tributyltinthiophene in the presence of a Pd catalyst and the subsequent oxidative ring-closing reactions led to target compounds in moderate to good yields.
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References
- 1 Handbook of Thiophene-based Materials, Applications in Organic Electronics and Photonics. Vol. 1 and 2. Perepichka IF. Perepichka DF. Wiley; West Sussex (UK): 2009
- 2 Deng P. Wu B. Lei Y. Cao H. Ong BS. Macromolecules 2016; 49: 2541
- 3 Li Z. Xu X. Zhang W. Meng X. Genene Z. Ma W. Mammo W. Yartsev A. Anderson MR. Janssen RA. Wang E. Energy Environ. Sci. 2017; 10: 2212
- 4 Usta H. Lu G. Facchetti A. Marks T. J. Am. Chem. Soc. 2006; 128: 9034
- 5 Amb CM. Chen S. Graham KR. Subbiah J. Small CE. So F. Reynolds JR. J. Am. Chem. Soc. 2011; 133: 10062
- 6 Coffin RC. Peet J. Rogers J. Bazan GC. Nat. Chem. 2009; 1: 657
- 7a Guo X. Puniredd SR. Baumgarten M. Pisula W. Mullen K. J. Am. Chem. Soc. 2012; 134: 8404
- 7b Guo X. Puniredd SR. Baumgarten M. Pisula W. Mullen K. Adv. Mater. 2013; 25: 5467
- 7c Keshtov ML. Sharma GD. Kuklin SA. Ostapov IE. Godovsky DY. Khokhlov AR. Chen FC. Polymer 2015; 65: 193
- 7d Garcia-Benito I. Zimmermann I. Urieta-Mora J. Arago J. Molina-Ontoria A. Orti E. Martin N. Nazeeruddin K. J. Mater. Chem. A 2017; 5: 8317
- 8a Dahlmann U. Neidlein R. Helv. Chim. Acta 1997; 80: 111
- 8b Guo X. Wang S. Enkelmann V. Baumgarten M. Mullen K. Org. Lett. 2011; 13: 6062
- 9 Keshtov ML. Kuklin SA. Osipov SN. Topchii MA. Konstantinov IO. Gamov AL. Khokhlov AR. Doklady Chem. 2015; 460: 50
- 10a Chen T. Pan G.-B. Wettach H. Fritzsche M. Höger S. Wan L.-J. Yang H.-B. Northrop BH. Stang PJ. J. Am. Chem. Soc. 2010; 132: 1328
- 10b Jiang L. Engle JT. Sirk L. Hartley CS. Ziegler CJ. Wang H. Org. Lett. 2011; 13: 3020
- 10c Xiao S. Zhou H. You W. Macromolecules 2008; 41: 5688
- 10d Brusso JL. Hirst OD. Dadvand A. Ganesan S. Cicoira F. Robertson CM. Oakley RT. Rosei F. Perepichka DF. Chem. Mater. 2008; 20: 2484
- 10e Schubert M. Trosien S. Schulz L. Brandscheid C. Schollmeyer D. Waldvogel SR. Eur. J. Org. Chem. 2014; 7091