TIPS-TTF as a precursor of low-symmetry TTF derivatives: Steric protection strategy in the regioselective C-H modification of TTF

Chemistry - A European Journal

Volumn 19, Issue 22, 2013, Pages 7156-7161

  Ueno, Ryota ^a   Fujino, Daishi ^a   Yorimitsu, Hideki ^a,b   Osuka, Atsuhiro ^a  

^a KYOTO UNIVERSITY   (Japan)

^b JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

Author keywords

C H modification; heterocycles; palladium; regioselectivity; steric hindrance

Indexed keywords

C-H MODIFICATION; FUNCTIONALIZATIONS; HETEROCYCLES; PALLADIUM-CATALYZED; REGIO-SELECTIVE; STERIC HINDRANCES; STERIC PROTECTION; TTF DERIVATIVES;

CHEMISTRY; PALLADIUM; SYNTHESIS (CHEMICAL);

REGIOSELECTIVITY;

EID: 84878032856     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201300623     Document Type: Article

References (90)

1. TTF Chemistry (Eds.:, J. Yamada, T. Sugimoto,), Kodansha, Tokyo, 2004
2. T. Otsubo, K. Takimiya, Bull. Chem. Soc. Jpn. 2004, 77, 43
3. A. Gorgues, P. Hudhomme, M. Salle, Chem. Rev. 2004, 104, 5151
4. M. Bendikov, F. Wudl, D. F. Perepichka, Chem. Rev. 2004, 104, 4891
5. J. L. Segura, N. Martín, Angew. Chem. 2001, 113, 1416
6. Angew. Chem. Int. Ed. 2001, 40, 1372
7. J. Yamada, H. Akutsu, H. Nishikawa, K. Kikuchi, Chem. Rev. 2004, 104, 5057
8. S. Horiuchi, H. Yamochi, G. Saito, K. Sakaguchi, M. Kusunoki, J. Am. Chem. Soc. 1996, 118, 8604
9. F. Pointillart, T. Cauchy, O. Maury, Y.-L. Gal, S. Golhen, O. Cador, L. Ouahab, Chem. Eur. J. 2010, 16, 11926
10. G. Saito, Y. Yoshida, Bull. Chem. Soc. Jpn. 2007, 80, 1
11. D. Jérome, Chem. Rev. 2004, 104, 5565
12. M. Iyoda, M. Hasegawa, Y. Miyake, Chem. Rev. 2004, 104, 5085
13. nd ed., (Eds.: L. Paquette, D. Crich, P L. Fuchs, G. Molander,), Wiley, Weinheim, 2009, p 9379.
14. D. C. Green, Ann. N. Y. Acad. Sci. 1978, 313, 361
15. D. C. Green, J. Org. Chem. 1979, 44, 1476
16. D. C. Green, J. Chem. Soc. Chem. Commun. 1977, 161
17. J. Garían, Adv. Heterocycl. Chem. 1995, 62, 249.
18. E. Aharon-Shalom, J. Y. Becker, J. Bernstein, S. Bittner, S. Shaik, Tetrahedron Lett. 1985, 26, 2783
19. J. Y. Becker, J. Bernstein, S. Bittner, L. Shahal, S. S. Shaik, J. Chem. Soc. Chem. Commun. 1991, 92
20. M. R. Bryce, G. Cooke, Synthesis 1991, 263.
21. A. Saad, O. Jeannin, M. Fourmigué, Tetrahedron 2011, 67, 3820
22. K. Lincke, M. A. Christensen, F. Diederich, M. B. Nielsen, Helv. Chim. Acta 2011, 94, 1743
23. M. Hasegawa, Y. Sone, S. Iwata, H. Matsuzawa, Y. Mazaki, Org. Lett. 2011, 13, 4688
24. T. Ito, K. Nakamura, T. Shirahata, T. Kawamoto, T. Mori, Y. Misaki, Chem. Lett. 2011, 40, 81
25. M. Ashizawa, K. Ishidzu, M. Watanabe, T. Tanahashi, T. Shirahata, T. Kawamoto, T. Mori, Y. Misaki, Chem. Lett. 2010, 39, 1093
26. A. S. Andersson, L. Kerndrup, A. O. Madsen, K. Kilså, M. B. Nielsen, J. Org. Chem. 2009, 74, 375
27. F. Biaso, M. Geoffroy, E. Canadell, P. Auban-Senzier, E. Levillain, M. Fourmigué, N. Avarvari, Chem. Eur. J. 2007, 13, 5394
28. A. S. Andersson, K. Kilså, T. Hassenkam, J.-P. Gisselbrecht, C. Boudon, M. Gross, M. B. Nielsen, F. Diederich, Chem. Eur. J. 2006, 12, 8451.
29. M. Narita, C. U. Pittman, Jr., Synthesis 1976, 489
30. A. Krief, Tetrahedron 1986, 42, 1204.
31. C. Rücker, Chem. Rev. 1995, 95, 1009
32. P. G. M. Wuts, T. W. Greene, Protective Groups in Organic Synthesis, 4 th ed., Wiley, Hoboken, 2007.
33. D. Alberico, M. E. Scott, M. Lautens, Chem. Rev. 2007, 107, 174
34. T. Satoh, M. Miura, Chem. Lett. 2007, 36, 200
35. A. Mori, A. Sugie, Bull. Chem. Soc. Jpn. 2008, 81, 548
36. T. Satoh, M. Miura, Synthesis 2010, 3395
37. L. Ackermann, R. Vicente, A. R. Kapdi, Angew. Chem. 2009, 121, 9976
38. Angew. Chem. Int. Ed. 2009, 48, 9792
39. D. Lapointe, K. Fagnou, Chem. Lett. 2010, 39, 1118
40. K. Hirano, M. Miura, Synlett 2011, 294
41. C-H Activation (Eds., J.-Q. Yu, Z. Shi,), Springer, Heidelberg, 2010
42. O. Daugulis, V. G. Zaitsev, D. Shabashov, Q.-N. Pham, A. Lazareva, Synlett 2006, 3382
43. I. V. Seregin, V. Gevorgyan, Chem. Soc. Rev. 2007, 36, 1173
44. J. Wencel-Delord, T. Droge, F. Liu, F. Glorius, Chem. Soc. Rev. 2011, 40, 4740
45. L. Ackermann, Chem. Rev. 2011, 111, 1315
46. T. W. Lyons, M. S. Sanford, Chem. Rev. 2010, 110, 1147
47. D. A. Colby, R. G. Bergman, J. A. Ellman, Chem. Rev. 2010, 110, 624
48. X. Chen, K. M. Engle, D.-H. Wang, J.-Q. Yu, Angew. Chem. 2009, 121, 5196
49. Angew. Chem. Int. Ed. 2009, 48, 5094
50. G. P. McGlacken, L. M. Bateman, Chem. Soc. Rev. 2009, 38, 2447
51. F. Kakiuchi, T. Kochi, Synthesis 2008, 3013
52. J. Yamaguchi, A. D. Yamaguchi, K. Itami, Angew. Chem. 2012, 124, 9092
53. Angew. Chem. Int. Ed. 2012, 51, 8960
54. M. N. Hopkinson, J. Wencel-Delord, F. Glorius, Angew. Chem. 2012, 124, 10382
55. Angew. Chem. Int. Ed. 2012, 51, 10236
56. J. J. Mousseau, A. B. Charette, Acc. Chem. Res. 2013, 46, 412
57. H. Yorimitsu, A. Osuka, Asian J. Org. Chem. 2013, 2, in press, doi: 10.1002/ajoc.201200183.
58. Y. Mitamura, H. Yorimitsu, K. Oshima, A. Osuka, Chem. Sci. 2011, 2, 2017.
59. M. Iwasaki, H. Yorimitsu, K. Oshima, Chem. Asian J. 2007, 2, 1430
60. Y. Kawamata, S. Tokuji, H. Yorimitsu, A. Osuka, Angew. Chem. 2011, 123, 9029
61. Angew. Chem. Int. Ed. 2011, 50, 8867
62. T. Niwa, H. Yorimitsu, K. Oshima, Org. Lett. 2007, 9, 2373
63. T. Niwa, H. Yorimitsu, K. Oshima, Org. Lett. 2008, 10, 4689
64. S. Tokuji, T. Yurino, N. Aratani, H. Shinokubo, A. Osuka, Chem. Eur. J. 2009, 15, 12208
65. S. Nakazono, S. Easwaramoorthi, D. Kim, H. Shinokubo, A. Osuka, Org. Lett. 2009, 11, 5426
66. K. Osawa, N. Aratani, A. Osuka, Tetrahedron Lett. 2009, 50, 3333.
67. A. Mori, A. Sekiguchi, K. Masui, T. Shimada, M. Horie, K. Osakada, M. Kawamoto, T. Ikeda, J. Am. Chem. Soc. 2003, 125, 1700
68. M. Takahashi, K. Masui, H. Sekiguchi, N. Kobayashi, A. Mori, M. Funahashi, N. Tamaoki, J. Am. Chem. Soc. 2006, 128, 10930
69. K. Masui, A. Mori, K. Okano, K. Takamura, M. Kinoshita, T. Ikeda, Org. Lett. 2004, 6, 2011
70. N. Masuda, S. Tanba, A. Sugie, D. Monguchi, N. Koumura, K. Hara, A. Mori, Org. Lett. 2009, 11, 2297
71. J. Shikuma, A. Mori, K. Matsui, R. Matsuura, A. Sekiguchi, H. Ikegami, M. Kawamoto, T. Ikeda, Chem. Asian J. 2007, 2, 301
72. S. Tamba, S. Tanaka, Y. Okubo, H. Meguro, S. Okamoto, A. Mori, Chem. Lett. 2011, 40, 398
73. A. Mori, J. Synth. Org. Chem. Jpn. 2011, 69, 1202
74. A. Yokooji, T. Satoh, M. Miura, M. Nomura, Tetrahedron 2004, 60, 6757
75. M. Miyasaka, A. Fukushima, T. Satoh, K. Hirano, M. Miura, Chem. Eur. J. 2009, 15, 3674
76. Q. Wang, R. Takita, Y. Kikuzaki, F. Ozawa, J. Am. Chem. Soc. 2010, 132, 11420
77. J. Hassan, E. Schulz, C. Gozzi, M. Lemaire, J. Mol. Catal. A J. Mol. Catal. A: Chem. 2003, 195, 125
78. P. Amaladass, J. A. Clement, A. K. Mohanakrishnan, Tetrahedron 2007, 63, 10363
79. P. Berrouard, A. Najari, A. Pron, D. Gendron, P.-O. Morin, J.-R. Pouliot, J. Veilleux, M. Leclerc, Angew. Chem. 2012, 124, 2110
80. Angew. Chem. Int. Ed. 2012, 51, 2068
81. C.-Y. Liu, H. Zhao, H.-h. Yu, Org. Lett. 2011, 13, 4068
82. F. Derridj, J. Roger, S. Djebbar, H. Doucet, Org. Lett. 2010, 12, 4320
83. S. Tamba, Y. Okubo, S. Tanaka, D. Monguchi, A. Mori, J. Org. Chem. 2010, 75, 6998
84. S. Yanagisawa, K. Ueda, H. Sekizawa, K. Itami, J. Am. Chem. Soc. 2009, 131, 14622
85. Application of our direct arylation of TTF:, T. C. Narayan, T. Miyakai, S. Seki, M. Dincǎ, J. Am. Chem. Soc. 2012, 134, 12932.
86. B. L. Bray, P. H. Mathies, R. Naef, D. R. Solas, T. T. Tidwell, D. R. Artis, J. M. Muchowski, J. Org. Chem. 1990, 55, 6317
87. J. Takagi, K. Sato, J. F. Hartwig, T. Ishiyama, N. Miyaura, Tetrahedron Lett. 2002, 43, 5649
88. E. M. Beck, N. P. Grimster, R. Hatley, M. J. Gaunt, J. Am. Chem. Soc. 2006, 128, 2528.
89. 3, see:, M. Miura, S. Pivsa-Art, G. Dyker, J. Heiermann, T. Satoh, M. Nomura, Chem. Commun. 1998, 1889.
90. T. Mori, H. Inokuchi, A. M. Kini, J. M. Williams, Chem. Lett. 1990, 19, 1279.