A selective and direct synthesis of 2-bromo-4-alkylthiophenes: Convenient and straightforward approaches for the synthesis of head-to-tail (HT) and tail-to-tail (TT) dihexyl-2,2′-bithiophenes

Tetrahedron Letters

Volumn 51, Issue 34, 2010, Pages 4526-4529

  El Shehawy, Ashraf A ^a,b   Abdo, Nabiha I ^a,c   El Barbary, Ahmed A ^c   Lee, Jae Suk ^a  

^a Gwangju Institute of Science and Technology (GIST)   (South Korea)

^b Kafrelsheikh University   (Egypt)

^c Tanta University   (Egypt)

Author keywords

2,2 Bithophenes; Alkylthiophenes; Bromination; Dihexylbithiophenes; Grignard reagents; HH and TT cross couplings; Kumada and Suzuki cross couplings

Indexed keywords

2 BROMO 3 HEXYLTHIOPHENE; 2 BROMO 4 ALKYLTHIOPHENE DERIVATIVE; 2 BROMO 4 HEXYLTHIOPHENE; 3 BUTYLTHIOPHENE; 3 HEXYLTHIOPHENE; 3,4' DIHEXYL 2,2' BITHIOPHENE DERIVATIVE; 4,4' DIHEXYL 2,2' BITHIOPHENE; DIHEXYL 2,2' BITHIOPHENE DERIVATIVE; THIOPHENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; SUZUKI REACTION; SYNTHESIS;

EID: 77955708348     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2010.06.100     Document Type: Article

References (59)

1. (a) D. Fichou J. Mater. Chem. 10 2000 571 588
2. (b) T. Otsubo, Y. Aso, and K. Takimiya J. Mater. Chem. 12 2002 2565 2575
3. (c) G. Barbarella Electron. Opt. Prop. Conjug. Mol. Syst. Conden. Phases 2003 79 97
4. (d) S. Hotta, Y. Ichino, and Y. Yoshida Electron. Opt. Prop. Conjug. Mol. Syst. Conden. Phases 2003 615 635
5. (e) S. Hotta Trans. Mater. Res. Soc. Jpn. 29 2004 985 990
6. (f) D.K. James, and J.M. Tour Top. Curr. Chem. 257 2005 33 62
7. (g) T. Otsubo, Y. Aso, and K. Takimiya Pure Appl. Chem. 77 2005 2003 2010
8. (h) I.F. Perepichka, D.F. Perepichka, H. Meng, and F. Wudl Adv. Mater. 17 2005 2281 2305
9. (i) J. Locklin, M. Roberts, S. Mannsfeld, and Z. Bao Polym. Rev. 46 2006 79 101
10. (j) A.R. Murphy, and J.M. Frechet J. Chem. Rev. 107 2007 1066 1096
11. (k) I. Osaka, and R.D. Mccullough Acc. Chem. Res. 41 2008 1202 1214
12. (l) A.L. Briseno, T.W. Holcombe, A.I. Boukai, E.C. Garnett, S.W. Shelton, J.J.M. Fréchet, and P. Yang Nano Lett. 10 2010 334 340
13. (a) J. Kowalik, L.M. Tolbert, S. Narayan, and A.S. Abhiraman Macromolecules 34 2001 5471 5479
14. (b) L.H. Nguyen, H. Hoppe, T. Erb, S. Günes, G. Gobsch, and N.S. Sariciftci Adv. Funct. Mater. 17 2007 1071 1078
15. (c) R. Singh, J. Kumar, R.K. Singh, R.C. Rastogi, and V. Kumar New J. Phys. 9 2007 40 61
16. (d) S. Günes, H. Neugebauer, and N.S. Sariciftci Chem. Rev. 107 2007 1324 1338
17. (e) S. Günes, D. Baran, G. Günbas, F. Özyurt, A. Fuchsbauer, N.S. Sariciftci, and L. Toppare Sol. Energy Mater. Sol. Cells 92 2008 1162 1169
18. (f) P.-T. Wu, H. Xin, F.S. Kim, G. Ren, and S.A. Jenekhe Macromolecules 42 2009 8817 8826
19. (g) C.-G. Wu, C.-Y. Lai, and N.-L. Hsiao Eur. Polym. J. 45 2009 879 887
20. (h) M. Lanzi, and L. Paganin React. Funct. Polym. 70 2010 346 360
21. (a) S. Pal, and A.K. Nandi Macromolecules 36 2003 8426 8432
22. (b) M. Al-Ibrahim, H.-K. Roth, M. Schroedner, A. Konkin, U. Zhokhavets, G. Gobsch, P. Scharff, and S. Sensfuss Org. Electron. 6 2005 65 77
23. (c) S. Vandeleene, K.V. Bergh, T. Verbiest, and G. Koeckelberghs Macromolecules 41 2008 5123 5131
24. (d) P. Arosio, M. Moreno, A. Famulari, G. Raos, M. Catellani, and S.V. Meille Chem. Mater. 21 2009 78 87
25. (e) W. Cai, X. Gong, and Y. Cao Sol. Energy Mat. Sol. Cells 94 2010 114 127
26. (a) M. Trznadel, A. Porn, M. Zagorska, R. Chrzaszcz, and J. Pielichowski Macromolecules 31 1998 5051 5058
27. (b) Y.-M. Chou, W.-H. Chen, and C.-C. Liang J. Mol. Struct. Theor. Chem. 894 2009 117 120
28. (a) M. Sato, and H. Morii Macromolecules 24 1991 1196 1200
29. (b) M. Sato, and H. Morii Polym. Commun. 32 1991 436 438
30. (c) M. ZagSrska, and I. Kulszewicz-Bajer Synth. Met. 45 1991 385 393
31. (d) T.-A. Chen, and R.D. Rieke J. Am. Chem. Soc. 114 1992 10087 10088
32. (e) G. Louarn, J. Kruszka, and S. Lefrant Synth. Met. 61 1993 233 238
33. (f) G. Barbarella, A. Bongini, and M. Zambianchi Macromolecules 27 1994 3039 3045
34. (g) T.-A. Chen, X. Wu, and R.D. Rieke J. Am. Chem. Soc. 117 1995 233 244
35. (h) F. Andreani, L. Angiolini, V. Grenci, and E. Salatelli Synth. Met. 145 2004 221 227
36. R.S. Loewe, P.C. Ewbank, J. Liu, L. Zhai, and R.D. McCullough Macromolecules 34 2001 4324 4333
37. M. Jeffries-El, G. Sauvé, and R.D. McCullough Macromolecules 38 2005 10346 10352
38. (a) M. Kumada, K. Tamao, and K. Sumitani Org. Synth. 58 1978 127 131
39. (b) T. Tamao, S. Komada, I. Nakajima, and M. Kumada Tetrahedron 28 1982 3347 3354
40. (c) C. van Pham, A. Burkhardt, R. Shabana, D.D. Cunningham, H.B. Mark Jr, and H. Zimmer Phosphorous, Sulfur Silicon Relat. Elem. 46 1989 153 168
41. (d) H. Zimmer, R. Shabana, A. Galal, H.B. Mark Jr., S. Gronowitz, and A.B. Hörnfeldt Phosphorous, Sulfur Silicon Relat. Elem. 42 1989 171 176
42. T. Beryozkina, V. Senkovskyy, E. Kaul, and A. Kiriy Macromolecules 41 2008 7817 7823
43. (a) N. Miyaura, T. Ishiyama, H. Sasaki, M. Ishikawa, M. Satoh, and A. Suzuki J. Am. Chem. Soc. 111 1989 314 321
44. (b) S. Guillerez, and G. Bidan Synth. Met. 93 1998 123 126
45. (a) J.-C. Li, S.-H. Lee, Y.-B. Hahn, K.-J. Kim, K. Zongb, and Y.-S. Lee Synth. Met. 158 2008 150 156
46. (b) J.-C. Li, H.-Y. Lee, S.-H. Lee, K. Zong, S.-H. Jin, and Y.-S. Lee Synth. Met. 159 2009 201 208
47. H. Kong, D.S. Chung, I.-N. Kang, E. Lim, Y.K. Jung, J.-H. Park, C.E. Park, and H.-K. Shim Bull. Korean Chem. Soc. 28 2007 1945 1950
48. (a) R.D. McCullough, R.D. Lowe, M. Jayaraman, and D.L. Anderson J. Org. Chem. 58 1993 904 912
49. (b) K.J. Hoffmann, and P.H.J. Carlsen Synth. Commun. 29 1999 1607 1610
50. (c) A. Yokoyama, R. Miyakoshi, and T. Yokozawa Macromolecules 37 2004 1169 1171
51. P.A. Chaloner, S.R. Gunatunga, and P.B. Hitchcock J. Chem. Soc., Perkin Trans. 2 1997 1597 1604
52. (a) R.M. Kellogg, A.P. Schaap, E.T. Harper, and H. Wynbert J. Org. Chem. 33 1968 2902 2909
53. (b) M.G. Reinecke, H.W. Adickes, and C. Pyun J. Org. Chem. 36 1971 2690 2692
54. (c) R.H. Mitchell, Y.-H. Lai, and R.V. Williams J. Org. Chem. 44 1979 4733 4735
55. (d) A. de Meijere, L. Zhao, V.N. Belov, M. Bossi, M. Noltemeyer, and S.W. Hell Chem. Eur. J. 13 2007 2503 2516
56. (e) S.D. Boyd, A.K.-Y. Jen, and C.K. Luscombe Macromolecules 42 2009 9387 9389
57. T. Dohi, K. Morimoto, C. Ogawa, H. Fujioka, and Y. Kita Chem. Pharm. Bull. 57 2009 710 713
58. T. Yamamoto, A. Morita, Y. Miyazaki, T. Maruyama, H. Wakayama, Z.-H. Zhou, Y. Nakamura, T. Kanbara, S. Sasaki, and K. Kubota Macromolecules 25 1992 1214 1223
59. T. Kirschbaum, C.A. Briehn, and P. Bäuerle J. Chem. Soc., Perkin Trans. 1 2000 1211 1216