Enantioselective synthesis and enhanced circularly polarized luminescence of S-shaped double azahelicenes

Journal of the American Chemical Society

Volumn 136, Issue 15, 2014, Pages 5555-5558

  Nakamura, Kyosuke ^a   Furumi, Seiichi ^b,c   Takeuchi, Masayuki ^c   Shibuya, Tetsuro ^a   Tanaka, Ken ^a,b  

^a TOKYO UNIVERSITY OF AGRICULTURE AND TECHNOLOGY   (Japan)

^b JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

^c NATIONAL INSTITUTE FOR MATERIALS SCIENCE   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMISTRY; SYNTHESIS (CHEMICAL);

CIRCULARLY POLARIZED LUMINESCENCE; ENANTIOSELECTIVE SYNTHESIS; HYDROARYLATION; S-SHAPED;

ENANTIOSELECTIVITY;

EID: 84898960513     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja500841f     Document Type: Article

References (65)

1. Peng, Z.; Takenaka, N. Chem. Rec. 2013, 13, 28
2. Shen, Y.; Chen, C.-F. Chem. Rev. 2012, 112, 1463
3. Amemiya, R.; Yamaguchi, M. Chem. Rec. 2008, 8, 116
4. Rajca, A.; Miyasaka, M. In Functional Organic Materials: Syntheses, Strategies, and Applications: Müller, T. J. J.; Bunz, U. H. F., Eds.; Wiley-VCH: Weinheim, Germany, 2007,: p 543.
5. Nuckolls, C.; Shao, R. F.; Jang, W. G.; Clark, N. A.; Walba, D. M.; Katz, T. J. Chem. Mater. 2002, 14, 773
6. Katz, T. J. Angew. Chem., Int. Ed. 2000, 39, 1921
7. Grimme, S.; Harren, J.; Sobanski, A.; Vögtle, F. Eur. J. Org. Chem. 1998, 1491
8. Nakai, Y.; Mori, T.; Sato, K.; Inoue, Y. J. Phys. Chem. A 2013, 117, 5082
9. Nakai, Y.; Mori, T.; Inoue, Y. J. Phys. Chem. A 2013, 117, 83
10. Nakai, Y.; Mori, T.; Inoue, Y. J. Phys. Chem. A 2012, 116, 7372
11. Gingras, M.; Félix, G.; Peresutti, R. Chem. Soc. Rev. 2013, 42, 1007
12. Gingras, M. Chem. Soc. Rev. 2013, 42, 968
13. Stará, I. G.; Starý, I. In Science of Synthesis; Siegel, J. S.; Tobe, Y., Eds.; Thieme: Stuttgart, 2010; Vol. 45b, p 885.
14. Urbano, A. Angew. Chem., Int. Ed. 2003, 42, 3986
15. Schmuck, C. Angew. Chem., Int. Ed. 2003, 42, 2448
16. Very recently, a large Cotton effect in the circular dichroism of an S-shaped double carbohelicene was observed in experimental and theoretical investigations. See: Ikenosako, M.; Nakai, Y.; Mori, T.; Fukuhara, G.; Inoue, Y. 93th Annual Meeting of The Chemical Society of Japan 2013, 3A2-15
17. Laarhoven, W. H.; Cuppen, Th. J. H. M. Recl. Tray. Chim. Pays-Bas. 1973, 92, 553
18. Martin, R. H.; Eynels, Ch.; Defay, N. Tetrahedron Lett. 1972, 27, 2731
19. Laarhoven, W. H.; Cuppen, Th. J. H. M. Tetrahedron Lett. 1971, 163
20. For a review, see: Transition-Metal-Mediated Aromatic Ring Construction; Tanaka, K., Ed.; Wiley: Hoboken, NJ, 2013.
21. Tanaka, K.; Kamisawa, A.; Suda, T.; Noguchi, K.; Hirano, M. J. Am. Chem. Soc. 2007, 129, 12078
22. Tanaka, K.; Fukawa, N.; Suda, T.; Noguchi, K. Angew. Chem., Int. Ed. 2009, 48, 5470
23. Fukawa, N.; Osaka, T.; Noguchi, K.; Tanaka, K. Org. Lett. 2010, 12, 1324
24. Sawada, Y.; Furumi, S.; Takai, A.; Takeuchi, M.; Noguchi, K.; Tanaka, K. J. Am. Chem. Soc. 2012, 134, 4080
25. Crittall, M. R.; Fairhurst, N. W. G.; Carbery, D. R. Chem. Commun. 2012, 48, 11181
26. Stará, I. G.; Starý, I.; Kollárovič, A.; Teplý, F.; Vyskočil, Š.; Šaman, D. Tetrahedron Lett. 1999, 40, 1993
27. Teplý, F.; Stará, I. G.; Starý, I.; Kollárovič, A.; Šaman, D.; Vyskočil, Š.; Fiedler, P. J. Org. Chem. 2003, 68, 5193
28. Jančařik, A.; Rybáček, J.; Cocq, K.; Chocholoušová, J. V.; Vacek, J.; Pohl, R.; Bednárová , L.; Fiedler, P.; Cisařová, I.; Stará, I.; Starý, I. Angew. Chem., Int. Ed. 2013, 52, 9970
29. Heller, B.; Hapke, M.; Fischer, C.; Andronova, A.; Starý, I.; Stará, I. J. Organomet. Chem. 2013, 723, 98
30. Shibata, T.; Uchiyama, T.; Yoshinami, Y.; Takayasu, S.; Tachikawa, K.; Endo, K. Chem. Commun. 2012, 48, 1311
31. Grandbois, A.; Collins, S. K. Chem.-Eur. J. 2008, 14, 9323
32. Caeiro, J.; Peña, D.; Cobas, A.; Pérez, D.; Guitián, E. Adv. Synth. Catal. 2006, 348, 2466
33. Miyasaka, M.; Rajca, A.; Pink, M.; Rajca, S. J. Am. Chem. Soc. 2005, 127, 13806
34. Carreño, M. C.; González-López, M.; Urbano, A. Chem. Commun. 2005, 611
35. Rajca, A.; Miyasaka, M.; Pink, M.; Wang, H.; Rajca, S. J. Am. Chem. Soc. 2004, 126, 15211
36. Carreño, M. C.; García-Cerrada, S.; Urbano, A. Chem.-Eur. J. 2003, 9, 4118
37. Kaneko, E.; Matsumoto, Y.; Kamikawa, K. Chem.-Eur. J. 2013, 19, 11837
38. Lin, W.; Dou, G.-L.; Hu, M.-H.; Cao, C.-P.; Huang, Z.-B.; Shi, D.-Q. Org. Lett. 2013, 15, 1238
39. Yang, Y.; Correa da Costa, R.; Fuchter, M. J.; Campbell, A. J. Nat. Photonics 2013, 7, 634
40. Yang, Y.; Correa da Costa, R.; Smilgies, D.-M.; Campbell, A. J.; Fuchter, M. J. Adv. Mater. 2013, 25, 2624
41. Oyama, H.; Nakano, K.; Harada, T.; Kuroda, R.; Naito, M.; Nobusawa, K.; Nozaki, K. Org. Lett. 2013, 15, 2104
42. Yamamoto, K.; Okazumi, M.; Suemune, H.; Usui, K. Org. Lett. 2013, 15, 1806
43. Weimar, M.; Correa da Costa, R.; Lee, F.-H.; Fuchter, M. J. Org. Lett. 2013, 15, 1706
44. Storch, J.; Bernard, M.; Sýkora, J.; Karvan, J.; Čermák, J. Eur. J. Org. Chem. 2013, 260
45. Storch, J.; Čermák, J.; Karban, J.; Cisařová, I.; Sýkora, J. J. Org. Chem. 2010, 75, 3137
46. Storch, J.; Sýkora, J.; Čermák, J.; Karban, J.; Cisařová, I.; Růžička, A. J. Org. Chem. 2009, 74, 3090
47. Shibuya, T.; Shibata, Y.; Noguchi, K.; Tanaka, K. Angew. Chem., Int. Ed. 2011, 50, 3963
48. Shibuya, T.; Nakamura, K.; Tanaka, K. Beilstein J. Org. Chem. 2011, 7, 944
49. Byers, P. M.; Rashid, J. I.; Mohamed, R. K.; Alabugin, I. V. Org. Lett. 2012, 14, 6032
50. Chen, C.-C.; Yang, S.-C.; Wu, M.-J. J. Org. Chem. 2011, 76, 10269
51. Hirano, K.; Inaba, Y.; Talasu, K.; Oishi, S.; Takemoto, Y.; Fujii, N.; Ohno, H. J. Org. Chem. 2011, 76, 9068
52. Hirano, K.; Inaba, Y.; Watanabe, T.; Oishi, S.; Fujii, N.; Ohno, H. Adv. Synth. Catal. 2010, 352, 368
53. Wang, W.; Hammond, G. B.; Xu, B. J. Am. Chem. Soc. 2012, 134, 5697
54. Wand, D.; Cai, R.; Sharma, S.; Jirak, J.; Thummanapelli, S. K.; Akhmedov, N. G.; Zhang, H.; Liu, X.; Petersen, J. L.; Shi, X. J. Am. Chem. Soc. 2012, 134, 9012
55. Gupta, S.; Koley, D.; Ravikumar, K.; Kundu, B. J. Org. Chem. 2013, 78, 8624
56. Homs, A.; Escofet, I.; Echavarren, A. M. Org. Lett. 2013, 15, 5782
57. Zhang, Y.; Yang, X.; Yao, Q.; Ma, D. Org. Lett. 2012, 14, 3056
58. Goto, K.; Yamaguchi, R.; Hiroto, S.; Ueno, H.; Kawai, T.; Shinokubo, H. Angew. Chem., Int. Ed. 2012, 51, 10333
59. Waghray, D.; Cloet, A.; Hecke, K. V.; Mertens, S. F. L.; Feyter, S. D.; Meervelt, L. V.; Van der Auweraer, M.; Dehaen, W. Chem.-Eur. J. 2013, 19, 12077
60. Morisaki, Y.; Gon, M.; Sasamori, T.; Tokitoh, N.; Chujo, Y. J. Am. Chem. Soc. 2014, 136, 3350
61. Maeda, H.; Hane, W.; Bando, Y.; Terashima, Y.; Haketa, Y.; Shibaguchi, H.; Kawai, T.; Naito, M.; Takaishi, K.; Uchiyama, M.; Muranaka, A. Chem.-Eur. J. 2013, 19, 16263
62. Kumar, J.; Nakashima, T.; Tsumatori, H.; Mori, M.; Naito, M.; Kawai, T. Chem.-Eur. J. 2013, 19, 14090
63. Maeda, H.; Bando, Y.; Shimomura, K.; Yamada, I.; Naito, M.; Nobusawa, K.; Tsumatori, H.; Kawai, T. J. Am. Chem. Soc. 2011, 133, 9266
64. Kaseyama, T.; Furumi, S.; Zhang, X.; Tanaka, K.; Takeuchi, M. Angew. Chem., Int. Ed. 2011, 50, 3684
65. Tsumatori, H.; Nakashima, T.; Kawai, T. Org. Lett. 2010, 12, 2362