Cyclization of 1,4-phenylenediacrylic acid with thionyl chloride and subsequent Suzuki-Miyaura reactions revisited. the products are benzo[1,2-b;5,6-b′]dithiophenes and not benzo[1,2-b;4,5-b′] dithiophenes

Advanced Synthesis and Catalysis

Volumn 354, Issue 4, 2012, Pages 731-739

  Hassan, Zahid ^a   Reimann, Sebastian ^a   Wittler, Kai ^a   Ludwig, Ralf ^a   Villinger, Alexander ^a   Langer, Peter ^a  

^a UNIVERSITY OF ROSTOCK   (Germany)

Author keywords

catalysis; cyclization; dithiophenes; heterocycles; palladium; regioselectivity; structure revision

Indexed keywords

EID: 84858022381     PISSN: 16154150     EISSN: 16154169     Source Type: Journal    
DOI: 10.1002/adsc.201100668     Document Type: Article

References (31)

1. S.-J. Jeong, R. Higuchi, T. Miyamoto, M. Ono, M. Kuwano, S. F. Mawatari, J. Nat. Prod. 2002, 65, 1344
2. T. R. Kelly, Y. Fu, J. T. Sieglen, H. de Silva, Org. Lett. 2000, 2, 2351.
3. F. Garnier, Angew. Chem. 1989, 101, 529
4. Angew. Chem. Int. Ed. Engl. 1989, 28, 513
5. F. Garnier, A. Yassar, R. Hajlaoui, G. Horowitz, F. Deloffre, B. Servet, S. Ries, P. Alnot, J. Am. Chem. Soc. 1993, 115, 8716
6. F. Garnier, R. Hajlaoui, A. Yassar, P. Srivastava, Science 1994, 265, 1684
7. A. Dodabalapur, L. Torsi, H. E. Katz, Science 1995, 268, 270
8. A. Dodabalapur, L. J. Rothberg, A. W. P. Fung, H. E. Katz, Science 1996, 272, 1462.
9. H. E. Katz, Z. Bao, S. L. Gilat, Acc. Chem. Res. 2001, 34, 359
10. K. Takimiya, Y. Kunugi, T. Otsubo, Chem. Lett. 2007, 36, 578
11. A. R. Murphy, J. M. J. Frechet, Chem. Rev. 2007, 107, 1066
12. B. S. Ong, Y. Wu, Y. Li, P. Liu, H. Pan, Chem. Eur. J. 2008, 14, 4766
13. S. Allard, M. Forster, B. Souharce, H. Thiem, U. Schert, Angew. Chem. 2008, 120, 4138
14. Angew. Chem. Int. Ed. 2008, 47, 4070
15. J. Chen, A. Y. Cao, Acc. Chem. Res. 2009, 42, 1709.
16. M. Miyasaka, K. Hirano, T. Satoh, M. Miura, Adv. Synth. Catal. 2009, 351, 2683.
17. W. Ried, G. Oremek, Liebigs Ann. Chem. 1980, 1172.
18. M. Malesevic, G. Karminski-Zamola, M. Bajic, D. W. Boykin, Heterocycles 1995, 41, 2691.
19. T. Higa, A. J. Krubsack, J. Org. Chem. 1975, 40, 3037; the use of catalytic amounts of pyridine resulted in a decrease of the reaction time
20. W. Ried, G. Oremek, B. Ocakcioglu, Liebigs Ann. Chem. 1980, 1424.
21. N. Miyaura, A. Suzuki, Chem. Rev. 1995, 95, 2457
22. A. Suzuki, J. Organomet. Chem. 1999, 576, 147
23. N. Miyaura, in: Advances in Metal-Organic Chemistry, (Ed.:, L. S. Liebeskind,), JAI, London, 1998, Vol. 6, pp 187- 243
24. A. Suzuki, in: Metal-Catalyzed Cross-Coupling Reactions, (Eds.:, F. Diederich, P. J. Stang,), Wiley-VCH, New York, 1998; Chapter 2
25. S. P. Stanforth, Tetrahedron 1998, 54, 263.
26. J. Kumagai, K. Hirano, T. Satoh, S. Seki, M. Miura, J. Phys. Chem. B: 2011, 115, 8446.
27. M. S. Simon, J. B. Rogers, W. Saenger, J. Z. Gougoutas, J. Am. Chem. Soc. 1967, 89, 5838.
28. M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G. A. Petersson, H. Nakatsuji, M. Caricato, X. Li, H. P. Hratchian, A. F. Izmaylov, J. Bloino, G. Zheng, J. L. Sonnenberg, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, J. A. Montgomery, Jr., J. E. Peralta, F. Ogliaro, M. Bearpark, J. J. Heyd, E. Brothers, K. N. Kudin, V. N. Staroverov, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J. C. Burant, S. S. Iyengar, J. Tomasi, M. Cossi, N. Rega, N. J. Millam, M. Klene, J. E. Knox, J. B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, R. L. Martin, K. Morokuma, V. G. Zakrzewski, G. A. Voth, P. Salvador, J. J. Dannenberg, S. Dapprich, A. D. Daniels, Ö. Farkas, J. B. Foresman, J. V. Ortiz, J. Cioslowski, D. J. Fox, Gaussian 09, Revision A.1, Gaussian, Inc., Wallingford CT, 2009
29. A.-D. Becke, J. Chem. Phys. 1993, 98, 5648
30. C. Lee, W. Yang, R. G. Parr, Phys. Rev. B: 1988, 37, 785
31. E. D. Glendening, A. E. Reed, J. E. Carpenter, F. Weinhold, NBO Version 3.1.