Synthesis of methylene-bridge polyarenes through palladium-catalyzed activation of benzylic carbon-hydrogen bond

Advanced Synthesis and Catalysis

Volumn 352, Issue 18, 2010, Pages 3267-3274

  Hsiao, Chien Chi ^a   Lin, Yi Kuan ^a   Liu, Chia Ju ^a   Wu, Tsun Cheng ^a   Wu, Yao Ting ^a  

^a NATIONAL CHENG KUNG UNIVERSITY   (Taiwan)

Author keywords

C H bond activation; fluorenes; indenofluorenes; NHC ligands; palladium; polyarenes

Indexed keywords

EID: 78650332146     PISSN: 16154150     EISSN: 16154169     Source Type: Journal    
DOI: 10.1002/adsc.201000651     Document Type: Article

References (107)

1. R. G. Harvey, Polycyclic Aromatic Hydrocarbons, Wiley-VCH, New York, 1997.
2. For reviews, see
3. K. D. Belfield, S. Yao, M. V. Bondar, Adv. Polym. Sci. 2008, 213, 97
4. J. U. Wallace, S. H. Chen, Adv. Polym. Sci. 2008, 212, 145
5. A. C. Grimsdale, K. Müllen, Macromol. Rapid Commun. 2007, 28, 1676
6. G. Hughes, M. R. Bryce, J. Mater. Chem. 2005, 15, 94
7. U. Scherf, E. J. W. List, Adv. Mater. 2002, 14, 477
8. M. T. Bernius, M. Inbasekaran, J. O'Brien, W. Wu, Adv. Mater. 2000, 12, 1737.
9. Y. Ie, Y. Umemoto, M. Nitani, Y. Aso, Pure Appl. Chem. 2008, 80, 589
10. C. Gadermaier, L. Luer, A. Gambetta, T. Virgili, M. Zavelani-Rossi, G. Lanzani, in: Semiconducting Polymers, (Eds.:, G. Hadziioannou, G. G. Malliaras,), 2nd edn., Wiley-VCH, Weinheim, 2007, pp 205.
11. O. Inganas, F. Zhang, M. R. Andersson, Acc. Chem. Res. 2009, 42, 1731
12. D. Jones, Org. Photovoltaics 2008, 57
13. G. Dennler, M. C. Scharber, C. J. Brabec, Adv. Mater. 2009, 21, 1323.
14. Fluorene, 2-halo- and 2,7-dihalo-substituted fluorenes are commercially available at reasonable prices. Generation of functional groups at other positions has to be processed with many steps, see
15. A. Tsuge, T. Yamasaki, T. Moriguchi, T. Matsuda, Y. Nagano, H. Nago, S. Mataka, S. Kajigaeshi, M. Tashiro, Synthesis 1993, 205
16. S. Kajigaeshi, T. Kadowaki, A. Nishida, S Fujisaki, Bull. Chem. Soc. Jpn. 1986, 59, 97
17. A. K. Sarkar, A. Chatterjee, B. Bandyopadhyay, Tetrahedron 1976, 32, 65. For a recent review for synthesis of fluorenes, see
18. S. Toyota, T. Iwanaga, in: Science of Synthesis, Georg Thieme Verlag, Stuttgart, Vol. 45b, p 818.
19. For the synthesis of (heteroatom-substituted) fluorenes not through the metal-catalyzed C-H activation, see
20. M. Tobisu, Y. Kita, Y. Ano, N. Chatani, J. Am. Chem. Soc. 2008, 130, 15982
21. I. A. Kashulin, I. E. Nifant′ev, J. Org. Chem. 2004, 69, 5476
22. Y.-S. Song, S. D. Kong, S. A. Khan, B. R. Yoo, I. N. Jung, Organometallics 2001, 20, 5586
23. W. Kirmse, K. Kund, E. Ritzer, A. E. Dorigo, K. N. Houk, J. Am. Chem. Soc. 1986, 108, 6045
24. D. L. J. Clive, R. Sunasee, Org. Lett. 2007, 9, 2677
25. K. Boeckmann, F. Vögtle, Chem. Ber. 1981, 114, 1065.
26. For reviews of aryl C-H bond activation, see
27. E. M. Beccalli, G. Broggini, M. Martinelli, S. Sottocornola, Chem. Rev. 2007, 107, 5318
28. D. Alberico, M. E. Scott, M. Lautens, Chem. Rev. 2007, 107, 174
29. J. Hassan, M. Sévignon, C. Gozzi, E. Schulz, M. Lemaire, Chem. Rev. 2002, 102, 1359
30. P. W. N. M. van Leeuwen, J. G. de Vries, in: Handbook of C-H Transformations, (Ed.:, G. Dyker,), Wiley-VCH, Weinheim, 2005, p 203
31. Y. Fujiwara, C. Jia, Pure Appl. Chem. 2001, 73, 319
32. F. Kakiuchi, N. Chatani, Adv. Synth. Catal. 2003, 345, 1077
33. V. Ritleng, C. Sirlin, M. Pfeffer, Chem. Rev. 2002, 102, 1731
34. F. Kakiuchi, S. Murai, Acc. Chem. Res. 2002, 35, 826
35. 3)-H bond activation, see
36. X. Chen, K. M. Engle, D.-H. Wang, J.-Q. Yu, Angew. Chem. 2009, 121, 5196
37. Angew. Chem. Int. Ed. 2009, 48, 5094
38. O. Daugulis, H.-Q. Do, D. Shabashov, Acc. Chem. Res. 2009, 42, 1074.
39. B. M. Trost, Angew. Chem. 1995, 107, 285
40. Angew. Chem. Int. Ed. Engl. 1995, 34, 259.
41. Several protocols involving metal-catalyzed functionalization of the benzylic C-H bond with the subsequent C-C bond formation have been reported. Pd
42. T. Kesharwani, R. C. Larock, Tetrahedron 2008, 64, 6090
43. J.-I. Inoh, T. Satoh, S. Pivsa-Art, M. Miura, M. Nomura, Tetrahedron Lett. 1998, 39, 4673. Pt
44. S. Yang, Z. Li, X. Jian, C. He, Angew. Chem. 2009, 121, 4059
45. Angew. Chem. Int. Ed. 2009, 48, 3999. Pt and Ru
46. M. Tobisu, H. Nakai, N. Chatani, J. Org. Chem. 2009, 74, 5471. Cu
47. T. Matsumoto, K. Ohkubo, K. Honda, A. Yazawa, H. Furutachi, S. Fujinami, S. Fukuzumi, M. Suzuki, J. Am. Chem. Soc. 2009, 131, 9258. Fe
48. Y.-Z. Li, B.-J. Li, X.-Y. Lu, S. Lin, Z.-J. Shi, Angew. Chem. 2009, 121, 3875
49. Angew. Chem. Int. Ed. 2009, 48, 3817
50. C.-X. Song, G.-X. Cai, T. R. Farrell, Z.-P. Jiang, H. Li, L.-B. Gan, Z.-J. Shi, Chem. Commun. 2009, 6002.
51. F. Wang, W. Ueda, Chem. Eur. J. 2009, 15, 742
52. L.-C. Campeau, M. Parisien, A. Jean, K. Fagnou, J. Am. Chem. Soc. 2006, 128, 581
53. M. Shimizu, K. Mochida, T. Hiyama, Angew. Chem. 2008, 120, 9906
54. Angew. Chem. Int. Ed. 2008, 47, 9760
55. K. Fuchibe, T. Akiyama, J. Am. Chem. Soc. 2006, 128, 1434.
56. S. J. Hwang, H. J. Kim, S. Chang, Org. Lett. 2009, 11, 4588.
57. In a crowded environment, the C-H bond in a methyl group can be activated, see
58. M. Chaumontet, R. Piccardi, N. Audic, J. Hitce, J.-L. Peglion, E. Clot, O. Baudoin, J. Am. Chem. Soc. 2008, 130, 15157
59. O. Baudoin, A. Herrbach, F. Guéritte, Angew. Chem. 2003, 115, 5914
60. Angew. Chem. Int. Ed. 2003, 42, 5736
61. W. A. Herrmann, C. Broßmer, K. Öfele, C.-P. Reisinger, T. Priermeier, M. Beller, H. Fischer, Angew. Chem. 1995, 107, 1989
62. Angew. Chem. Int. Ed. Engl. 1995, 34, 1844
63. G. Dyker, J. Org. Chem. 1993, 58, 6426
64. G. Dyker, Angew. Chem. 1994, 106, 117
65. Angew. Chem. Int. Ed. Engl. 1994, 33, 103
66. G. Dyker, Angew. Chem. 1992, 104, 1079
67. Angew. Chem. Int. Ed. Engl. 1992, 31, 1023.
68. C.-G. Dong, Q.-S. Hu, Tetrahedron 2008, 64, 2537
69. C.-G. Dong, Q.-S. Hu, Angew. Chem. 2006, 118, 2347
70. Angew. Chem. Int. Ed. 2006, 45, 2289.
71. T.-P. Liu, C.-H. Xing, Q.-S. Hu, Angew. Chem. 2010, 122, 2971
72. 4 could not improve unsatisfactory results. Our optimal condition is also inefficient for this tandem reaction.
73. Reviews for NHC ligands
74. S. Diez-Gonzalez, N. Marion, S. P. Nolan, Chem. Rev. 2009, 109, 3612
75. O. Schuster, L. Yang, H. G. Raubenheimer, M. Albrecht, Chem. Rev. 2009, 109, 3445
76. M. Poyatos, J. A. Mata, E. Peris, Chem. Rev. 2009, 109, 3677
77. N-Heterocyclic Carbenes in Synthesis, (Ed.:, S. P. Nolan,), Wiley-VCH, Weinheim, 2006.
78. 13C NMR and mass spectra.
79. 3)-H activation, see:, M. Lafrance, S. I. Gorelsky, K. Fagnou, J. Am. Chem. Soc. 2007, 129, 14570.
80. a=32), the benzylic proton in 1d should be more acidic than those in 1a and 1c, see
81. F. G. Bordwell, D. Algrim, N. R. Vanier, J. Org. Chem. 1977, 42, 1817
82. F. G. Bordwell, W. S. Matthews, N. R. Vanier, J. Am. Chem. Soc. 1975, 97, 442.
83. 3)-H activation gave a similar result, see:, M. Chaumontet, R. Piccardi, N. Audic, J. Hitce, J.-L. Peglion, N. Audic, J. Hitce, J.-L. Peglion, E. Clot, O. Baudoin, J. Am. Chem. Soc. 2008, 130, 1515.
84. For conventional protocols for synthesizing indenofluorene 11, see
85. S. Merlet, M. Birau, Z. Y. Wang, Org. Lett. 2002, 4, 2157. Indenofluorene 11 and its derivatives have been applied as semiconductors and blue organic electroluminescent devices
86. T.-C. Lin, C.-S. Hsu, C.-L. Hu, Y.-F. Chen, W.-J. Huang, Tetrahedron Lett. 2009, 50, 182
87. C. Poriel, J. J. Liang, J. Rault-Berthelot, F. Barriere, N. Cocherel, A. M. Z. Slawin, D. Horhant, M. Virboul, G. Alcaraz, N. Audebrand, L. Vignau, N. Huby, G. Wantz, L. Hirsch, Chem. Eur. J. 2007, 13, 10055
88. K. Wong, L. Chi, S. Huang, Y. Liao, L. Y. Wang, Org. Lett. 2006, 8, 5029
89. T. Hadizad, J. Zhang, Z. Y. Wang, T. C. Gorjanc, C. Py, Org. Lett. 2005, 7, 795.
90. A conventional protocol for synthesizing indenofluorene 13, see:, M. Shimizu, Y. Tomioka, I. Nagao, T. Hiyama, Synlett 2009, 3147.
91. Synthesis of indenes through metal-catalyzed coupling reactions of haloarenes with alkynes, see
92. D. A. Alonso, C. Nájera, M. C. Pacheco, Adv. Synth. Catal. 2002, 344, 172
93. D. K. Rayabarapu, C.-H. Cheng, Chem. Commun. 2002, 942
94. C.-C. Liu, R. P. Korivi, C.-H. Cheng, Chem. Eur. J. 2008, 14, 9503
95. L. G. Quan, V. Gevorgyan, Y. Yamamoto, J. Am. Chem. Soc. 1999, 121, 3545
96. A. A. Pletnev, Q. Tian, R. C. Larock, J. Org. Chem. 2002, 67, 9276
97. D. K. Rayabarapu, C.-H. Yang, C.-H. Cheng, J. Org. Chem. 2003, 68, 6726
98. K.-J. Chang, D. K. Rayabarapu, C.-H. Cheng, Org. Lett. 2003, 5, 3963
99. D. Zhang, E. K. Yum, Z. Liu, R. C. Larock, Org. Lett. 2005, 7, 4963
100. R. Deng, L. Sun, Z. Li, Org. Lett. 2007, 9, 5207.
101. X-ray crystallographic data can be obtained free of charge from the Cambridge Crystallographic Data Centre via.
102. G. R. Desiraju, A. Gavezzotti, J. Chem. Soc. Chem. Commun. 1989, 621
103. C. A. Hunter, J. K. M. Sanders, J. Am. Chem. Soc. 1990, 112, 5525
104. L. L. Miller, K. R. Mann, Acc. Chem. Res. 1996, 29, 417.
105. C. S. Frampton, K. S. Knight, N. Shankland, K. Shankland, J. Mol. Struct. 2000, 520, 29
106. Y. Kai, F. Hama, N. Yasuoka, N. Kasai, Acta Crystallogr. B: 1978, 34, 1263.
107. H. Sakurai, T. Daiko, T. Hirao, Science 2003, 301, 1878.