Thiophene-fused borepins as directly functionalizable boron-containing π-electron systems

Journal of the American Chemical Society

Volumn 136, Issue 19, 2014, Pages 7132-7139

  Levine, David R ^a   Siegler, Maxime A ^a   Tovar, John D ^a,b  

^a JOHNS HOPKINS UNIVERSITY   (United States)

^b Johns Hopkins University   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIZATION; ELECTROLYTIC REDUCTION; ELECTRONIC STRUCTURE; THIOPHENE;

CHEMICAL ROBUSTNESS; ELECTROCHEMICAL REDUCTIONS; ELECTRONIC DELOCALIZATION; ELECTROPHILIC AROMATIC SUBSTITUTIONS; MOLECULAR PROPERTIES; POLYCYCLIC AROMATICS; SPECTROSCOPIC RESPONSE; SYNTHETIC PROTOCOLS;

BORON;

DIBENZOBOREPIN DERIVATIVE; DITHIENOBOREPIN DERIVATIVE; FLUORIDE ION; LEWIS ACID; ORGANOBORON DERIVATIVE; POLYCYCLIC AROMATIC COMPOUND; THIOPHENE DERIVATIVE; UNCLASSIFIED DRUG;

AIR; ARTICLE; CHEMICAL MODIFICATION; CHEMICAL STRUCTURE; CONJUGATION; CONTROLLED STUDY; DIRECT FUNCTIONALIZATION; ELECTROCHEMICAL ANALYSIS; ELECTRON; ELECTRONIC STRUCTURE; ELECTROPHILIC AROMATIC SUBSTITUTION; ELECTROPHILICITY; ISOMER; METALATION; MOISTURE; MOLECULAR DIVERSIFICATION; MOLECULAR STABILITY; NUCLEAR MAGNETIC RESONANCE; PI ELECTRON; SPECTROSCOPY; SYNTHESIS; ULTRAVIOLET SPECTROSCOPY;

EID: 84900793186     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja502644e     Document Type: Article

References (95)

1. Fukazawa, A.; Yamaguchi, S. Chem. Asian J. 2009, 4, 1386-1400
2. Iida, A.; Yamaguchi, S. J. Am. Chem. Soc. 2011, 133, 6952-6955
3. Saito, S.; Matsuo, K.; Yamaguchi, S. J. Am. Chem. Soc. 2012, 134, 9130-9133
4. Wood, T. K.; Piers, W. E.; Keay, B. A.; Parvez, M. Chem. Eur. J. 2010, 16, 12199-12206
5. Araneda, J. F.; Neue, B.; Piers, W. E.; Parvez, M. Angew. Chem., Int. Ed. 2012, 51, 8546-8550
6. Hoffend, C.; Schödel, F.; Bolte, M.; Lerner, H.-W.; Wagner, M. Chem. Eur. J. 2012, 18, 15394-15405
7. Agou, T.; Kobayashi, J.; Kawashima, T. Org. Lett. 2006, 8, 2241-2244
8. Hatakeyama, T.; Hashimoto, S.; Oba, T.; Nakamura, M. J. Am. Chem. Soc. 2012, 134, 19600-19603
9. Matsumoto, F.; Chujo, Y. Macromolecules 2003, 36, 5516-5519
10. Rao, Y.-L.; Wang, S. Inorg. Chem. 2011, 50, 12263-12274
11. Kim, S.; Song, K.-H.; Kang, S. O.; Ko, J. Chem. Commun. 2004, 68-69
12. Tokitoh, N.; Wakita, K.; Okazaki, R.; Nagase, S.; Schleyer, P. v. R.; Jiao, H. J. Am. Chem. Soc. 1997, 119, 6951-6952
13. Lee, S. H.; Jang, B.-B.; Kafafi, Z. H. J. Am. Chem. Soc. 2005, 127, 9071-9078
14. Xu, C.; Yamada, H.; Wakamiya, A.; Yamaguchi, S.; Tamao, K. Macromolecules 2004, 37, 8978-8983
15. Usta, H.; Lu, G.; Facchetti, A.; Marks, T. J. J. Am. Chem. Soc. 2006, 128, 9034-9035
16. Mercier, L. G.; Furukawa, S.; Piers, W. E.; Wakamiya, A.; Yamaguchi, S.; Parvez, M.; Harrington, R. W.; Clegg, W. Organometallics 2011, 30, 1719-1729
17. Bouit, P. A.; Escande, A.; Szucs, R.; Szieberth, D.; Lescop, C.; Nyulászi, L.; Hissler, M.; Réau, R. J. Am. Chem. Soc. 2012, 134, 6524-6527
18. He, X.; Borau-Garcia, J.; Woo, A. Y. Y.; Trudel, S.; Baumgartner, T. J. Am. Chem. Soc. 2013, 135, 1137-1147
19. Worch, J. C.; Chirdon, D. N.; Maurer, A. B.; Qiu, Y.; Geib, S. J.; Bernhard, S.; Noonan, K. J. T. J. Org. Chem. 2013, 78, 7462-7469
20. Mishra, S. P.; Javier, A. E.; Zhang, R.; Liu, J.; Belot, J. A.; Osaka, I.; McCullough, R. D. J. Mater. Chem. 2011, 21, 1551-1561
21. Okamoto, T.; Kudoh, K.; Wakamiya, A.; Yamaguchi, S. Org. Lett. 2005, 7, 5301-5304
22. Ebata, H.; Miyazaki, E.; Yamamoto, T.; Takimiya, K. Org. Lett. 2007, 9, 4499-4502
23. Patra, A.; Wijsboom, Y. H.; Leitus, G.; Bendikov, M. Chem. Mater. 2011, 23, 896-906
24. Gibson, G. L.; McCormick, T. M.; Seferos, D. S. J. Am. Chem. Soc. 2012, 134, 539-547
25. Takimiya, K.; Kunugi, Y.; Konda, Y.; Niihara, N.; Otsubo, T. J. Am. Chem. Soc. 2004, 126, 5084-5085
26. Yamaguchi, S.; Akiyama, S.; Tamao, K. J. Organomet. Chem. 2002, 652, 3-9
27. Shefer, N.; Harel, T.; Rozen, S. J. Org. Chem. 2009, 74, 6993-6998
28. Durben, S.; Baumgartner, T. Inorg. Chem. 2011, 50, 6823-6836
29. Lorbach, A.; Bolte, M.; Li, H.; Lerner, H.-W.; Holthausen, M. C.; Jäkle, F.; Wagner, M. Angew. Chem., Int. Ed. 2009, 48, 4584-4588
30. Su, H.-C.; Fadhel, O.; Yang, C.-J.; Cho, T.-Y.; Fave, C.; Hissler, M.; Wu, C.-C.; Réau, R. J. Am. Chem. Soc. 2006, 128, 983-995
31. Ren, Y.; Baumgartner, T. J. Am. Chem. Soc. 2011, 133, 1328-1340
32. Wu, J.; Pisula, W.; Müllen, K. Chem. Rev. 2007, 107, 718-747
33. Anthony, J. E. Chem. Rev. 2006, 106, 5028-5048
34. Bunz, U. H. F. Chem. Eur. J. 2009, 15, 6780-6789
35. Dou, C.; Saito, S.; Matsuo, K.; Hisaki, I.; Yamaguchi, S. Angew. Chem., Int. Ed. 2012, 51, 12206-12210
36. Ren, Y.; Kan, W. H.; Henderson, M. A.; Bomben, P. G.; Berlinguette, C. P.; Thangadurai, V.; Baumgartner, T. J. Am. Chem. Soc. 2011, 133, 17014-17026
37. Ren, Y.; Kan, W. H.; Thangadurai, V.; Baumgartner, T. Angew. Chem., Int. Ed. 2012, 51, 3964-3968
38. Knack, D. H.; Marshall, J. L.; Harlow, G. P.; Dudzik, A.; Szaleniec, M.; Liu, S.-Y.; Heider, J. Angew. Chem., Int. Ed. 2013, 52, 2599-2601
39. Wang, X.-Y.; Lin, H.-R.; Lei, T.; Yang, D.-C.; Zhuan, F.-D.; Wang, J.-Y.; Yuan, S.-C.; Pei, J. Angew. Chem., Int. Ed. 2013, 52, 3117-3120
40. Wakita, K.; Tokitoh, N.; Okazaki, R.; Nagase, S.; Schleyer, P. v. R.; Jiao, H. J. Am. Chem. Soc. 1999, 121, 11336-11344
41. Karney, W. L.; Kastrup, C. J.; Oldfield, S. P.; Rzepa, H. S. J. Chem. Soc., Perkin Trans. 2 2002, 388-392
42. Iida, A.; Sekioka, A.; Yamaguchi, S. Chem. Sci. 2012, 3, 1461-1466
43. Jäkle, F. Chem. Rev. 2010, 110, 3985-4022
44. van Tamelen, E. E.; Brieger, G.; Untch, K. G. Tetrahedron Lett. 1960, 1, 14-15
45. Leusink, A. J.; Drenth, W.; Noltes, J. G.; van der Kerk, J. G. M. Tetrahedron Lett. 1967, 8, 1263-1266
46. Ashe, A. J., III; Kampf, J. W.; Kausch, C. M.; Konishi, H.; Kristen, M. O.; Kroker, J. Organometallics 1990, 9, 2944-2948
47. Mercier, L. G.; Piers, W. E.; Parvez, M. Angew. Chem., Int. Ed. 2009, 48, 6108-6111
48. Caruso, A., Jr.; Siegler, M. A.; Tovar, J. D. Angew. Chem., Int. Ed. 2010, 49, 4213-4217
49. Caruso, A., Jr.; Tovar, J. D. J. Org. Chem. 2011, 76, 2227-2239
50. Caruso, A., Jr.; Tovar, J. D. Org. Lett. 2011, 13, 3106-3109
51. Levine, D. R.; Caruso, A., Jr.; Siegler, M. A.; Tovar, J. D. Chem. Commun. 2012, 48, 6256-6258
52. Iida, A.; Saito, S.; Sasamori, T.; Yamaguchi, S. Angew. Chem., Int. Ed. 2013, 52, 3760-3764
53. Ashe, A. J., III; Kampf, J. W.; Nakadaira, Y.; Pace, J. M. Angew. Chem., Int. Ed. 1992, 31, 1255-1258
54. Ashe, A. J., III; Klein, W.; Rousseau, R. Organometallics 1993, 12, 3225-3231
55. Agou, T.; Kobayashi, J.; Kawashima, T. Chem. Commun. 2007, 3204-3206
56. Wakamiya, A.; Mishima, K.; Ekawa, K.; Yamaguchi, S. Chem. Commun. 2008, 579-581
57. Reus, C.; Weidlich, S.; Bolte, M.; Lerner, H.-W.; Wagner, M. J. Am. Chem. Soc. 2013, 135, 12892-12907
58. Rudebusch, G. E.; Zakharov, L. N.; Liu, S.-Y. Angew. Chem., Int. Ed. 2013, 52, 9316-9319
59. Shuto, A.; Kushida, T.; Fukushima, T.; Kaji, H.; Yamaguchi, S. Org. Lett. 2013, 15, 6234-6237
60. Gronowitz, S.; Yom-Tov, B.; Michael, U. Acta Chem. Scand. 1973, 27, 2257-2270
61. Gronowitz, S.; Gassne, P.; Yom-Tov, B. Acta Chem. Scand. 1969, 23, 2927-2930
62. Jeffries, A. T., III; Gronowitz, S. Chem. Scripta 1973, 4, 183-187
63. Sugihara, Y.; Yagi, T.; Murata, I. J. Am. Chem. Soc. 1992, 114, 1479-1481
64. Sugihara, Y.; Miyatake, R.; Yagi, T. Chem. Lett. 1993, 22, 933-936
65. Sugihara, Y.; Miyatake, R.; Yagi, T.; Murata, I.; Jinguji, M.; Nakazawa, T.; Imamura, A. Tetrahedron 1994, 50, 6495-6504
66. Jeffries, A. T., III; Párkányi, C. J. Phys. Chem. 1976, 80, 287-291
67. McCullough, R. D. Adv. Mater. 1998, 10, 93-116
68. Gronowitz, S.; Hoernfeldt, A.-B. Thiophenes; Elsevier Academic Press: Oxford, 2004.
69. Handbook of Thiophene-Based Materials: Applications in Organic Electronics and Photonics, Vols. 1 and 2; Perepichka, I. F.; Perepichka, D. F., Eds.; Wiley: Chichester, U.K., 2009.
70. Ngwendson, J. N.; Atemnkeng, W. N.; Schultze, C. M.; Banerjee, A. Org. Lett. 2006, 8, 4085-4088
71. 2. This compound was stable to atmospheric moisture and oxygen, but was sensitive to coordinating solvents: Caruso, Jr., A. Ph.D. Thesis, Johns Hopkins University, May 2011.
72. Schleyer, P. v. R.; Maerker, C.; Dransfeld, A.; Jiao, H.; Hommes, N. J. R. v. E. J. Am. Chem. Soc. 1996, 118, 6317-6318
73. Miyasaka, S.; Kobayashi, J.; Kawashima, T. Tetrahedron Lett. 2009, 50, 3467-3469
74. Subramanian, G.; Schleyer, P. v. R.; Jiao, H. Organometallics 1997, 16, 2362-2369
75. Doty, J. C.; Babb, B.; Grisdale, P. J.; Glogowski, M.; Williams, J. L. R. J. Organomet. Chem. 1972, 38, 229-236
76. Yamaguchi, S.; Akiyama, S.; Tamao, K. J. Am. Chem. Soc. 2000, 122, 6335-6336
77. Jäkle, F. Coord. Chem. Rev. 2006, 250, 1107-1121
78. Wade, C. R.; Broomsgrove, A. E. J.; Aldridge, S.; Gabbaï, F. P. Chem. Rev. 2010, 110, 3958-3984
79. Dimitrijević, E.; Taylor, M. S. ACS Catal. 2013, 3, 945-962
80. Pammer, F.; Jäkle, F. Chem. Sci. 2012, 3, 2598-2606
81. Hundertmark, T.; Littke, A. F.; Buchwald, S. L.; Fu, G. C. Org. Lett. 2000, 2, 1729-1731
82. Milstein, D.; Stille, J. K. J. Am. Chem. Soc. 1979, 101, 4992-4998
83. Skene, W. G.; Dufresne, S. Org. Lett. 2004, 6, 2949-2952
84. Lirag, R. C.; Osowska, K.; Miljanić, O. Š. Org. Biomol. Chem. 2012, 10, 4847-4850
85. Rowan, S. J.; Cantrill, S. J.; Cousins, G. R. L.; Sanders, J. K. M.; Stoddart, J. F. Angew. Chem., Int. Ed. 2002, 41, 898-952
86. Li, H.; Xu, Q.; Li, N.; Sun, R.; Ge, J.; Lu, J.; Gu, H.; Yan, F. J. Am. Chem. Soc. 2010, 132, 5542-5543
87. Gu, P.-Y.; Zhou, F.; Gao, J.; Li, G.; Wang, C.; Xu, Q.-F.; Zhang, Q.; Lu, J.-M. J. Am. Chem. Soc. 2013, 135, 14086-14089
88. Simão, C.; Mas-Torrent, M.; Casado-Montenegro, J.; Otón, F.; Veciana, J.; Rovira, C. J. Am. Chem. Soc. 2011, 133, 13256-13259
89. Scott, J. C.; Bozano, L. D. Adv. Mater. 2007, 19, 1452-1463
90. Yamaguchi, S.; Shirasaka, T.; Tamao, K. Org. Lett. 2000, 2, 4129
91. Zhou, G.; Baumgarten, M.; Müllen, K. J. Am. Chem. Soc. 2008, 130, 12477-12484
92. Prón, A.; Zhou, G.; Nourouzi-Arasi, H.; Baumgarten, M.; Müllen, K. Org. Lett. 2009, 11, 3550-3553
93. Sakuda, E.; Ando, Y.; Ito, A.; Kitamura, N. J. Phys. Chem. A 2010, 114, 9144-9150
94. Albota, M.; Beljonne, D.; Brédas, J.-L.; Ehrlich, J. E.; Fu, J.-Y.; Heikal, A. A.; Hess, S. E.; Kogej, T.; Levin, M. D.; Marder, S. E.; McCord-Maughon, D.; Perry, J. W.; Röckel, H.; Rumi, M.; Subramaniam, G.; Webb, W. W.; Wu, X.-L.; Xu, C. Science 1998, 281, 1653-1656
95. Collings, J. C.; Poon, S.-Y.; Le Droumaguet, C.; Charlot, M.; Katan, C.; Palsson, L.-O.; Beeby, A.; Mosely, J. A.; Kaiser, H. M.; Kaufmann, D.; Wong, W.-Y.; Blanchard-Desce, M.; Marder, T. B. Chem. Eur. J. 2009, 15, 198-208