Palladium-Assisted "Aromatic Metamorphosis" of Dibenzothiophenes into Triphenylenes

Angewandte Chemie - International Edition

Volumn 54, Issue 24, 2015, Pages 7162-7166

  Vasu, Dhananjayan ^a   Yorimitsu, Hideki ^a,b   Osuka, Atsuhiro ^a  

^a KYOTO UNIVERSITY   (Japan)

^b JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

Author keywords

C H arylation; C S cleavage; cross coupling; palladium; sulfur

Indexed keywords

AROMATIC COMPOUNDS; AROMATIZATION; CATALYSIS; CHEMICAL REACTIONS; PALLADIUM; STEEL BEAMS AND GIRDERS; SULFUR;

AROMATIC STRUCTURES; AROMATIC SULFUR COMPOUND; C-H ARYLATION; C-S CLEAVAGE; CROSS-COUPLINGS; ORGANOSULFUR COMPOUNDS; PALLADIUM-CATALYZED ARYLATION; PALLADIUM-CATALYZED REACTIONS;

SULFUR COMPOUNDS;

EID: 85027924637     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201501992     Document Type: Article

References (125)

1. A. Criado, M. Vilas-Varela, A. Cobas, D. Pérez, D. Peña, E. Guitián, J. Org. Chem. 2013, 78, 12637
2. X. Ding, S. T. Nguyen, J. D. Williams, N. P. Peet, Tetrahedron Lett. 2014, 55, 7002
3. S. P. J. T. Bachollet, J. F. Vivat, D. C. Cocker, H. Adams, J. P. A. Harrity, Chem. Eur. J. 2014, 20, 12889
4. S. Suzuki, Y. Segawa, K. Itami, J. Yamaguchi, Nat. Chem. 2015, 7, 227.
5. S. Chuprakov, F. W. Hwang, V. Gevorgyan, Angew. Chem. Int. Ed. 2007, 46, 4757
6. Angew. Chem. 2007, 119, 4841
7. T. Horneff, S. Chuprakov, N. Chernyak, V. Gevorgyan, V. V. Fokin, J. Am. Chem. Soc. 2008, 130, 14972
8. M. Miura, M. Yamauchi, M. Murakami, Chem. Commun. 2009, 1470
9. M. Miura, M. Yamauchi, M. Murakami, Org. Lett. 2008, 10, 3085
10. S. Chuprakov, S. W. Kwok, V. V. Fokin, J. Am. Chem. Soc. 2013, 135, 4652; for reviews, see
11. B. Chattopadhyay, V. Gevorgyan, Angew. Chem. Int. Ed. 2012, 51, 862
12. Angew. Chem. 2012, 124, 886
13. P. Anbarasan, D. Yadagiri, S. Rajasekar, Synthesis 2014, 46, 3004.
14. S. Gronowitz, A.-B. Hörnfeldt, Thiophenes, Elsevier, Oxford, 2004
15. E. Block, Advances in Sulfur Chemistry, JAI Press, Greenwich, 1994
16. R. J. Cremlyn, An Introduction of Organosulfur Chemistry, Wiley, Chichester, 1996
17. Organic Sulfur Chemistry: Biochemical Aspects (Eds.:, S. Oae, T. Okuyama,), CRC Press, Boca Raton, FL, 1992.
18. C. Song, Catal. Today 2003, 86, 211
19. I. V. Babich, J. A. Moulijn, Fuel 2003, 82, 607
20. R. T. Yang, A. Hernández-Maldonado, F. H. Yang, Science 2003, 301, 79.
21. E. Wenkert, T. W. Ferreira, E. L. Michelotti, J. Chem. Soc. Chem. Commun. 1979, 637
22. E. Wenkert, M. H. Leftin, E. L. Michelotti, J. Chem. Soc. Chem. Commun. 1984, 617
23. M. Tiecco, M. Tingoli, E. Wenkert, J. Org. Chem. 1985, 50, 3828
24. L. Hintermann, M. Schmitz, Y. Chen, Adv. Synth. Catal. 2010, 352, 2411.
25. Y. Li, T. Thiemann, T. Sawada, S. Mataka, M. Tashiro, J. Org. Chem. 1997, 62, 7926
26. T. Thiemann, H. Fujii, D. Ohira, K. Arima, Y. Li, S. Mataka, New J. Chem. 2003, 27, 1377; see also Ref. [1c] and [1d].
27. S. Laschat, A. Baro, N. Steinke, F. Giesselmann, C. Hägele, G. Scalia, R. Judele, E. Kapatsina, S. Sauer, A. Schreivogel, M. Tosoni, Angew. Chem. Int. Ed. 2007, 46, 4832
28. Angew. Chem. 2007, 119, 4916
29. S. Sergeyev, W. Pisula, Y. H. Geerts, Chem. Soc. Rev. 2007, 36, 1902
30. K. Togashi, S. Nomura, N. Yokoyama, T. Yasuda, C. Adachi, J. Mater. Chem. 2012, 22, 20689
31. H. Wettach, S. S. Jester, A. Colsmann, U. Lemmer, N. Rehmann, K. Meerholz, S. Höger, Synth. Met. 2010, 160, 691
32. R. Freudenmann, B. Behnisch, M. Hanack, J. Mater. Chem. 2001, 11, 1618
33. S. Tanaka, C. Adachi, T. Koyama, Y. Taniguchi, Chem. Lett. 1998, 975.
34. D. Pérez, E. Guitián, Chem. Soc. Rev. 2004, 33, 274
35. D. Pérez, D. Peña, E. Guitián, Eur. J. Org. Chem. 2013, 5981.
36. Y. Terao, H. Wakui, M. Nomoto, T. Satoh, M. Miura, M. Nomura, J. Org. Chem. 2003, 68, 5236
37. Z. Liu, X. Zhang, R. C. Larock, J. Am. Chem. Soc. 2005, 127, 15716
38. T. T. Jayanth, C.-H. Cheng, Chem. Commun. 2006, 894
39. Z. Liu, R. C. Larock, J. Org. Chem. 2007, 72, 223
40. I. Nagao, M. Shimizu, T. Hiyama, Angew. Chem. Int. Ed. 2009, 48, 7573
41. Angew. Chem. 2009, 121, 7709
42. A. A. Cant, L. Roberts, M. F. Greaney, Chem. Commun. 2010, 46, 8671
43. M. Shimizu, I. Nagao, Y. Tomioka, T. Kadowaki, T. Hiyama, Tetrahedron 2011, 67, 8014
44. M. Iwasaki, S. Iino, Y. Nishihara, Org. Lett. 2013, 15, 5326
45. K. Ozaki, K. Kawasumi, M. Shibata, H. Ito, K. Itami, Nat. Commun. 2015, 6, 6251.
46. J. Srogl, G. D. Allred, L. S. Liebeskind, J. Am. Chem. Soc. 1997, 119, 12376
47. S. Zhang, D. Marshall, L. S. Liebeskind, J. Org. Chem. 1999, 64, 2796
48. A. Zapf, Angew. Chem. Int. Ed. 2003, 42, 5394
49. Angew. Chem. 2003, 115, 5552
50. H. Lin, X. Dong, Y. Li, Q. Shen, L. Lu, Eur. J. Org. Chem. 2012, 4675.
51. S. R. Dubbaka, P. Vogel, Angew. Chem. Int. Ed. 2005, 44, 7674
52. Angew. Chem. 2005, 117, 7848
53. L. Wang, W. He, Z. Yu, Chem. Soc. Rev. 2013, 42, 599
54. S. G. Modha, V. P. Mehta, E. V. Van der Eycken, Chem. Soc. Rev. 2013, 42, 5042
55. F. Pan, Z.-J. Shi, ACS Catal. 2014, 4, 280
56. H. Prokopcová, C. O. Kappe, Angew. Chem. Int. Ed. 2008, 47, 3674
57. Angew. Chem. 2008, 120, 3732
58. E. C. Garnier-Amblard, L. S. Liebeskind, Boronic Acids, 2 nd ed., (Ed.: D. G. Hall,), Wiley-VCH, Weinheim, 2011, chap. 7.
59. Y. Ookubo, A. Wakamiya, H. Yorimitsu, A. Osuka, Chem. Eur. J. 2012, 18, 12690
60. K. Murakami, H. Yorimitsu, A. Osuka, Angew. Chem. Int. Ed. 2014, 53, 7510
61. Angew. Chem. 2014, 126, 7640
62. T. Sugahara, K. Murakami, H. Yorimitsu, A. Osuka, Angew. Chem. Int. Ed. 2014, 53, 9329
63. Angew. Chem. 2014, 126, 9483
64. S. Otsuka, D. Fujino, K. Murakami, H. Yorimitsu, A. Osuka, Chem. Eur. J. 2014, 20, 13146
65. A. Baralle, S. Otsuka, V. Guérin, K. Murakami, H. Yorimitsu, A. Osuka, Synlett 2015, 26, 327.
66. D. Alberico, M. E. Scott, M. Lautens, Chem. Rev. 2007, 107, 174
67. T. Satoh, M. Miura, Chem. Lett. 2007, 36, 200
68. L. C. Campeau, D. R. Stuart, K. Fagnou, Aldrichimica Acta 2007, 40, 35
69. I. V. Seregin, V. Gevorgyan, Chem. Soc. Rev. 2007, 36, 1173
70. L. C. Lewis, R. G. Bergman, J. A. Ellman, Acc. Chem. Res. 2008, 41, 1013
71. F. Kakiuchi, T. Kochi, Synthesis 2008, 3013
72. O. Daugulis, H.-Q. Do, D. Shabashov, Acc. Chem. Res. 2009, 42, 1074
73. A. A. Kulkarni, O. Daugulis, Synthesis 2009, 4087
74. X. Chen, K. M. Engle, D.-H. Wang, J.-Q. Yu, Angew. Chem. Int. Ed. 2009, 48, 5094
75. Angew. Chem. 2009, 121, 5196
76. L. Ackermann, R. Vicente, A. R. Kapdi, Angew. Chem. Int. Ed. 2009, 48, 9792
77. Angew. Chem. 2009, 121, 9976
78. F. Bellina, R. Rossi, Tetrahedron 2009, 65, 10269
79. C.-L. Sun, B.-J. Li, Z.-J. Shi, Chem. Commun. 2010, 46, 677
80. T. W. Lyons, M. S. Sanford, Chem. Rev. 2010, 110, 1147
81. A. Lei, W. Liu, C. Liu, M. Chen, Dalton Trans. 2010, 39, 10352
82. K. Hirano, M. Miura, Synlett 2011, 294
83. C. Liu, H. Zhang, W. Sui, A. Lei, Chem. Rev. 2011, 111, 1780
84. J. Wencel-Delord, T. Dröge, F. Liu, F. Glorius, Chem. Soc. Rev. 2011, 40, 4740
85. L. Ackermann, Chem. Rev. 2011, 111, 1315
86. J. Yamaguchi, A. D. Yamaguchi, K. Itami, Angew. Chem. Int. Ed. 2012, 51, 8960
87. Angew. Chem. 2012, 124, 9092
88. H. Yorimitsu, A. Osuka, Asian J. Org. Chem. 2013, 2, 356
89. F. Shibahara, T. Murai, Asian J. Org. Chem. 2013, 2, 624
90. G. Rouquet, N. Chatani, Angew. Chem. Int. Ed. 2013, 52, 11726
91. Angew. Chem. 2013, 125, 11942
92. R. Rossi, F. Bellina, M. Lessi, C. Manzini, Adv. Synth. Catal. 2014, 356, 17
93. M. He, J.-F. Soulé, H. Doucet, ChemCatChem 2014, 6, 1824
94. R. Rossi, F. Bellina, M. Lessi, C. Manzini, L. A. Perego, Synthesis 2014, 46, 2833
95. M. Miura, T. Satoh, K. Hirano, Bull. Chem. Soc. Jpn. 2014, 87, 751
96. Y. Segawa, T. Maekawa, K. Itami, Angew. Chem. Int. Ed. 2015, 54, 66
97. Angew. Chem. 2015, 127, 68.
98. K. K. Laali, J.-H. Chun, T. Okazaki, S. Kumar, G. L. Borosky, C. Swartz, J. Org. Chem. 2007, 72, 8383.
99. H. Kurosawa, S. Ogoshi, Y. Kawasaki, S. Murai, M. Miyoshi, I. Ikeda, J. Am. Chem. Soc. 1990, 112, 2813
100. J.-Y. Legros, J.-C. Fiaud, Tetrahedron Lett. 1990, 31, 7453
101. 4, see
102. Y. M. A. Yamada, T. Watanabe, T. Beppu, N. Fukuyama, K. Torii, Y. Uozumi, Chem. Eur. J. 2010, 16, 11311
103. J. Yan, Z. Zhou, M. Zhu, Synth. Commun. 2006, 36, 1495.
104. M. Matsumoto, H. Yoshioka, K. Nakatsu, T. Yoshida, S. Otsuka, J. Am. Chem. Soc. 1974, 96, 3322
105. A. F. Littke, C. Dai, G. C. Fu, J. Am. Chem. Soc. 2000, 122, 4020
106. C. Dai, G. C. Fu, J. Am. Chem. Soc. 2001, 123, 2719.
107. T. E. Barder, S. L. Buchwald, Org. Lett. 2004, 6, 2649.
108. Just before the submission of this manuscript, the palladium-catalyzed arylation of azoles or thiazoles with aryl sulfides was reported:, F. Zhu, Z.-X. Wang, Org. Lett. 2015, 17, 1601.
109. M. Catellani, G. P. Chiusoli, J. Organomet. Chem. 1992, 425, 151
110. S. Pivsa-Art, T. Satoh, Y. Kawamura, M. Miura, M. Nomura, Bull. Chem. Soc. Jpn. 1998, 71, 467
111. G. Dyker, Angew. Chem. Int. Ed. 1999, 38, 1698
112. Angew. Chem. 1999, 111, 1808
113. B. Martín-Matute, C. Mateo, D. J. Cárdenas, A. M. Echavarren, Chem. Eur. J. 2001, 7, 2341
114. B. S. Lane, M. A. Brown, D. Sames, J. Am. Chem. Soc. 2005, 127, 8050
115. V. Farina, in Comprehensive Organometallic Chemistry II, Vol. 12 (Eds.:, E. W. Abel, F. G. A. Stone, G. Wilkinson,), Pergamon, Oxford, 1995, chap. 3.4.
116. M. Gómez-Gallego, M. A. Sierra, Chem. Rev. 2011, 111, 4857.
117. L. H. S. Smith, S. C. Coote, H. F. Sneddon, D. J. Procter, Angew. Chem. Int. Ed. 2010, 49, 5832
118. Angew. Chem. 2010, 122, 5968
119. S. Akai, Y. Kita, Top. Curr. Chem. 2007, 274, 35
120. K. S. Feldman, Tetrahedron 2006, 62, 5003
121. S. K. Bur, A. Padwa, Chem. Rev. 2004, 104, 2401.
122. A. Haryono, K. Miyatake, J. Natori, E. Tsuchida, Macromolecules 1999, 32, 3146
123. H. Sirringhaus, R. H. Friend, C. Wang, J. Leuninger, K. Müllen, J. Mater. Chem. 1999, 9, 2095
124. T. Iwasaki, Y. Kohinata, H. Nishide, Org. Lett. 2005, 7, 755
125. S. Zhang, X. Qiao, Y. Chen, Y. Wang, R. M. Edkins, Z. Liu, H. Li, Q. Fang, Org. Lett. 2014, 16, 342.