Double elimination protocol for convenient synthesis of dihalodiphenylacetylenes: Versatile building blocks for tailor-made phenylene-ethynylenes

Advanced Synthesis and Catalysis

Volumn 346, Issue 7, 2004, Pages 767-776

  Orita, Akihiro ^a   Miyamoto, Kazuhiko ^a   Nakashima, Mikio ^a   Ye, Fangguo ^a   Otera, Junzo ^a  

^a OKAYAMA UNIVERSITY OF SCIENCE   (Japan)

Author keywords

Acetylene; Aldehydes; Double elimination; Halogen; Sulfone

Indexed keywords

ACETYLENE; ACETYLENE DERIVATIVE; AROMATIC COMPOUND; BENZALDEHYDE; BENZYL DERIVATIVE; CARBON; HALOGEN; PHENYL GROUP; SULFONE DERIVATIVE;

ARTICLE; CHEMICAL BOND; CHEMICAL COMPOSITION; CHEMICAL REACTION; CHEMICAL STRUCTURE; ELIMINATION REACTION; SYNTHESIS;

EID: 4143129841     PISSN: 16154150     EISSN: None     Source Type: Journal    
DOI: 10.1002/adsc.200404014     Document Type: Article

References (57)

1. a) S. Höger, V. Enkelmann, K. Bonrad, C. Tschierske, Angew. Chem. Int. Ed. 2000, 39, 2268;
2. b) C.-H. Lee, T. Yamamoto, Bull. Chem. Soc. Jpn. 2002, 75, 615;
3. c) C. Sekine, K. Iwakura, N. Konya, M. Minai, K. Fujisawa, Liquid Crystals 2001, 28, 1375;
4. d) D. J. Pesak, J. S. Moore, Angew. Chem. Int. Ed. Engl. 1997, 36, 1636.
5. a) A. Kokil, I. Shiyanovskaya, K. D. Singer, C. Weder, J. Am. Chem. Soc. 2002, 124, 9978;
6. b) Y. Morisaki, Y. Chujo, Chem. Lett. 2002, 194;
7. c) O. Mongin, L. Porrès, L. Moreaux, J. Mertz, M. Blanchard-Desce, Org. Lett. 2002, 4, 719.
8. For carbon anion, see: a) R. Boese, A. J. Matzger, K. P. C. Vollhardt, J. Am. Chem. Soc. 1997, 119, 2052; for polymers, see: b) D. A. M. Egbe, E. Birckner, E. Klemm, J. Polym. Sci. Part A: Polym. Chem. 2002, 40, 2670; c) P. K. Tsolakis, J. K. Kallitsis, A. Godt, Macromolecules 2002, 35, 5758; d) J. N. Wilson, W. Steffen, T. G. McKenzie, G. Lieser, M. Oda, D. Neher, U. H. F. Bunz, J. Am. Chem. Soc. 2002, 124, 6830.
9. For carbon anion, see: a) R. Boese, A. J. Matzger, K. P. C. Vollhardt, J. Am. Chem. Soc. 1997, 119, 2052; for polymers, see: b) D. A. M. Egbe, E. Birckner, E. Klemm, J. Polym. Sci. Part A: Polym. Chem. 2002, 40, 2670; c) P. K. Tsolakis, J. K. Kallitsis, A. Godt, Macromolecules 2002, 35, 5758; d) J. N. Wilson, W. Steffen, T. G. McKenzie, G. Lieser, M. Oda, D. Neher, U. H. F. Bunz, J. Am. Chem. Soc. 2002, 124, 6830.
10. For carbon anion, see: a) R. Boese, A. J. Matzger, K. P. C. Vollhardt, J. Am. Chem. Soc. 1997, 119, 2052; for polymers, see: b) D. A. M. Egbe, E. Birckner, E. Klemm, J. Polym. Sci. Part A: Polym. Chem. 2002, 40, 2670; c) P. K. Tsolakis, J. K. Kallitsis, A. Godt, Macromolecules 2002, 35, 5758; d) J. N. Wilson, W. Steffen, T. G. McKenzie, G. Lieser, M. Oda, D. Neher, U. H. F. Bunz, J. Am. Chem. Soc. 2002, 124, 6830.
11. For carbon anion, see: a) R. Boese, A. J. Matzger, K. P. C. Vollhardt, J. Am. Chem. Soc. 1997, 119, 2052; for polymers, see: b) D. A. M. Egbe, E. Birckner, E. Klemm, J. Polym. Sci. Part A: Polym. Chem. 2002, 40, 2670; c) P. K. Tsolakis, J. K. Kallitsis, A. Godt, Macromolecules 2002, 35, 5758; d) J. N. Wilson, W. Steffen, T. G. McKenzie, G. Lieser, M. Oda, D. Neher, U. H. F. Bunz, J. Am. Chem. Soc. 2002, 124, 6830.
12. a) K. Sonogashira, Y. Tohda, N. Hagihara, Tetrahedron Lett. 1975, 4467;
13. b) Y. Tohda, K. Sonogashira, N. Hagihara, Synthesis 1977, 777;
14. c) S. Takahashi, Y Kuroyama, K. Sonogashira, N. Hagihara, Synthesis 1980, 627;
15. d) K-y. Tomizaki, R. S. Loewe, C. Kirmaier, J. K. Schwartz, J. L. Retsek, D. F. Bocian, D. Holten, J. S. Lindsey, J. Org. Chem. 2002, 67, 6519;
16. e) R. E. Bauer, V. Enkelmann, U. M. Wiesler, A. J. Berresheim, K. Müllen, Chem. Eur. J. 2002, 8, 3858;
17. f) M. Lu, Y. Wei, B. Xu, C. F-C. Cheng, Z. Peng, D. R. Powell, Angew. Chem. Int. Ed. 2002, 41, 1566;
18. g) T. M. Pappenfus, K. R. Mann, Org. Lett. 2002, 4, 3043;
19. h) D. L. Pearson, J. M. Tour, J. Org. Chem. 1997, 62, 1376.
20. a) M. B. Nielsen, N. F. Utesch, N. N. P. Moonen, C. Boudon, J.-P. Gisselbrecht, S. Concilio, S. P. Piotto, P. Seiler, P. Günter, M. Gross, F. Diederich, Chem. Eur. J. 2002, 8, 3601;
21. b) H. S. Blanchette, S. C. Brand, H. Naruse, T. J. R. Weakley, M. M. Haley, Tetrahedron 2000, 56, 9581,
22. c) S. C. Ciulei, R. R. Tykwinski, Org. Lett. 2000, 2, 3607;
23. d) W. B. Wan, S. C. Brand, J. J. Pak, M. M. Haley, Chem. Eur. J. 2000, 6, 2044.
24. a) O. Henze, D. Lentz, A. D. Schlüter, Chem. Eur. J. 2000, 6, 2362;
25. for discrimination of arenyl iodide from chloride, see: b) M. Sonoda, A. Inaba, K. Itahashi, Y. Tobe, Org. Lett. 2001, 3, 2419.
26. a) F. Ye, A. Orita, A. Doumoto, J. Otera, Tetrahedron 2003, 59, 5635;
27. b) A. Orita, F. Ye, A. Doumoto, J. Otera, Chem. Lett. 2003, 32, 104;
28. c) A. Orita, D. Hasegawa, T. Nakano, J. Otera, Chem. Eur. J. 2002, 8, 2000;
29. d) A. Orita, D. L. An, T. Nakano, J. Yaruva, N. Ma, J. Otera, Chem. Eur. J. 2002, 8, 2005;
30. e) A. Orita, N. Yoshioka, P. Struwe, A. Braier, A. Beckmann, J. Otera, Chem. Eur. J. 1999, 5, 1355.
31. See Supporting Information. TLC analyses in the reaction of 3a with 4g and GC analysis of the crude products are shown.
32. a) T. Kawasaki, M. Somei, Heterocycles 1990, 31, 1605;
33. b M. Harmata, C. L. Barnes, Tetrahedron Lett. 1990, 31, 1825
34. G. Maerkl, G. Y. Jin, K.-P. Berr, Tetrahedron Lett. 1993, 34, 3103.
35. For review, see: a) N. Miyaura, A. Suzuki, Chem. Rev. 1995, 95, 2457; b) B. H. Ridgeway, K. D. Woerpel, J. Org. Chem. 1998, 63, 458; c) K. Matos, J. A. Soderquist, J. Org. Chem. 1998, 63, 461; d) S. Kotha, K. Lahiri, D. Kashinath Tetrahedron 2002, 58, 9633.
36. For review, see: a) N. Miyaura, A. Suzuki, Chem. Rev. 1995, 95, 2457; b) B. H. Ridgeway, K. D. Woerpel, J. Org. Chem. 1998, 63, 458; c) K. Matos, J. A. Soderquist, J. Org. Chem. 1998, 63, 461; d) S. Kotha, K. Lahiri, D. Kashinath Tetrahedron 2002, 58, 9633.
37. For review, see: a) N. Miyaura, A. Suzuki, Chem. Rev. 1995, 95, 2457; b) B. H. Ridgeway, K. D. Woerpel, J. Org. Chem. 1998, 63, 458; c) K. Matos, J. A. Soderquist, J. Org. Chem. 1998, 63, 461; d) S. Kotha, K. Lahiri, D. Kashinath Tetrahedron 2002, 58, 9633.
38. For review, see: a) N. Miyaura, A. Suzuki, Chem. Rev. 1995, 95, 2457; b) B. H. Ridgeway, K. D. Woerpel, J. Org. Chem. 1998, 63, 458; c) K. Matos, J. A. Soderquist, J. Org. Chem. 1998, 63, 461; d) S. Kotha, K. Lahiri, D. Kashinath Tetrahedron 2002, 58, 9633.
39. a) R. F. Heck, Org. React. 1982, 27, 345;
40. for reviews, see: b) R. F. Heck, Palladium Reagents in Organic Synthesis, Academic Press, London, 1985; c) L. E. Overman, Pure Appl. Chem. 1994, 66, 1423; d) E. de Meijere, F. E. Meyer, Angew. Chem. Int. Ed. 1994, 33, 2379; e) W. Cabri, I. Candiani, Acc. Chem. Res. 1995, 28, 2; f) I. P. Beletskaya, A. V. Cheprakov, Chem. Rev. 2000, 100, 3009.
41. for reviews, see: b) R. F. Heck, Palladium Reagents in Organic Synthesis, Academic Press, London, 1985; c) L. E. Overman, Pure Appl. Chem. 1994, 66, 1423; d) E. de Meijere, F. E. Meyer, Angew. Chem. Int. Ed. 1994, 33, 2379; e) W. Cabri, I. Candiani, Acc. Chem. Res. 1995, 28, 2; f) I. P. Beletskaya, A. V. Cheprakov, Chem. Rev. 2000, 100, 3009.
42. for reviews, see: b) R. F. Heck, Palladium Reagents in Organic Synthesis, Academic Press, London, 1985; c) L. E. Overman, Pure Appl. Chem. 1994, 66, 1423; d) E. de Meijere, F. E. Meyer, Angew. Chem. Int. Ed. 1994, 33, 2379; e) W. Cabri, I. Candiani, Acc. Chem. Res. 1995, 28, 2; f) I. P. Beletskaya, A. V. Cheprakov, Chem. Rev. 2000, 100, 3009.
43. for reviews, see: b) R. F. Heck, Palladium Reagents in Organic Synthesis, Academic Press, London, 1985; c) L. E. Overman, Pure Appl. Chem. 1994, 66, 1423; d) E. de Meijere, F. E. Meyer, Angew. Chem. Int. Ed. 1994, 33, 2379; e) W. Cabri, I. Candiani, Acc. Chem. Res. 1995, 28, 2; f) I. P. Beletskaya, A. V. Cheprakov, Chem. Rev. 2000, 100, 3009.
44. for reviews, see: b) R. F. Heck, Palladium Reagents in Organic Synthesis, Academic Press, London, 1985; c) L. E. Overman, Pure Appl. Chem. 1994, 66, 1423; d) E. de Meijere, F. E. Meyer, Angew. Chem. Int. Ed. 1994, 33, 2379; e) W. Cabri, I. Candiani, Acc. Chem. Res. 1995, 28, 2; f) I. P. Beletskaya, A. V. Cheprakov, Chem. Rev. 2000, 100, 3009.
45. a) E. Negishi, T. Takahashi, O. King, Org. Synth. 1987, 66, 67;
46. b) J. A. Miller, R. P. Farrell, Tetrahedron 1998, 54, 6441;
47. c) C. Dai, G. C. Fu, J. Am. Chem. Soc. 2001, 123, 2719;
48. d) G. Y. Li, J. Org. Chem. 2002, 67, 3643.
49. H. Gilman, F. K. Cartledge, J. Organomet. Chem. 1967, 2, 447.
50. D. R. Coulson, Inorg. Synth. 1972, 13, 121.
51. P. J. van Meurs, R. A. J. Janssen, J. Org. Chem. 2000, 65, 5712.
52. G. C. Bond, P. B. Wells, Journal of Catalysis 1965, 4, 211.
53. M. J. Mio, L. C. Kopel, J. B. Braun, T. L. Gadzikwa, K. L. Hull, R. G. Brisbois, C. J. Markworth, P. A. Grieco, Org. Lett. 2002, 4, 3199.
54. V. Mamane, I. Ledoux-Rak, S. Deveau, J. Zyss, O. Riant, Synthesis 2003, 455.
55. Y. Tobe, I. Ohki, M. Sonoda, H. Niino, T. Sato, T. Wakabayashi, J. Am. Chem. Soc. 2003, 125, 5614.
56. A. N. Novikov, M. G. Grigor'ev, V. N. Kalinin, N. I. Kobel'kova, E. S. Krongauz, A. P. Travnikova, Zhurnal obshchei Khimii, 1979, 49, 2121.
57. R. J. Gonzalo, J. Esquivias, A. Lafuente, C. Diaz, J. Org. Chem. 2003, 68, 8120.