Coordination-induced intramolecular double cyclization: Synthesis of boron-bridged dipyridylvinylenes and dithiazolylvinylenes

Synthesis

Volumn , Issue 1, 2009, Pages 127-132

  Zhao, Qiang ^a   Zhang, Hongyu ^a   Wakamiya, Atsushi ^a   Yamaguchi, Shigehiro ^a  

^a NAGOYA UNIVERSITY   (Japan)

Author keywords

Electron systems; Acetylene; Boron; Cascade cyclization; N heteroaryl

Indexed keywords

CASCADE CYCLIZATION; COORDINATION COMPLEXES; DERIVATIZATION; FLUORESCENCE SPECTRUM; INTENSE EMISSIONS; LADDER MOLECULES; N-HETEROARYL; PYRIDYL; REDUCTION POTENTIALS; REVERSIBLE REDUCTIONS; TERMINAL POSITIONS;

ACETYLENE; BORON; BORON COMPOUNDS; COORDINATION REACTIONS; CYCLIZATION; ELECTRONS; EMISSION SPECTROSCOPY; LIGHTING; OPTICAL SENSORS;

CYCLIC VOLTAMMETRY;

ACETYLENE DERIVATIVE; BIS(DIMESITYLBORYL); BROMINE DERIVATIVE; BROMODIBENZOBOROLE; DI(HETEROARYL)ACETYLENE; DI(HETEROARYL)VINYLENE; DIBENZOBOROLYL; DIPYRIDYLVINYLENE DERIVATIVE; DITHIAZOLYLVINYLENE DERIVATIVE; PYRIDINE DERIVATIVE; THIAZOLE; THIAZOLYL; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CONTROLLED STUDY; CRYSTAL STRUCTURE; CYCLIC POTENTIOMETRY; CYCLIZATION; ELECTROCHEMISTRY; ELECTRON; FLUORESCENCE ANALYSIS; REDUCTION KINETICS; SYNTHESIS;

EID: 63849154924     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0028-1083271     Document Type: Article

References (29)

1. (a) Craft, A.; Grimsdale, A. C.; Holmes, A. B. Angew. Chem. Int. Ed. 1998, 37, 402.
2. (b) Watson, M. D.; Fechtenkötter, A.; Müllen, K. Chem. Rev. 2001, 101, 1267.
3. (c) Anthony, J. E. Angew. Chem. Int. Ed. 2008, 47, 452.
4. Wakamiya, A.; Taniguchi, T.; Yamaguchi, S. Angew. Chem. Int. Ed. 2006, 45, 3170.
5. (a) Yoshino, J.; Kano, N.; Kawashima, T. Chem. Commun. 2007, 559.
6. (b) Jaska, C. A.; Piers, W. E.; McDonald, R.; Parvez, M. J. Org. Chem. 2007, 72, 5234.
7. (c) Ishida, N.; Narumi, M.; Murakami, M. Org. Lett. 2008, 10, 1279.
8. (d) Rao, Y.-L.; Amarne, H.; Zhao, S.-B.; McCormick, T. M.; Martić, S.; Sun, Y.; Wang, R.-Y.; Wang, S. J. Am. Chem. Soc. 2008, 130, 12898.
9. Yamaguchi, S.; Xu, C.; Okamoto, T. Pure Appl. Chem. 2006, 78, 721.
10. (a) Yamaguchi, S.; Xu, C.; Tamao, K. J. Am. Chem. Soc. 2003, 125, 13662.
11. (b) Xu, C.; Wakamiya, A.; Yamaguchi, S. Org. Lett. 2004, 6, 3707.
12. (c) Xu, C.; Wakamiya, A.; Yamaguchi, S. J. Am. Chem. Soc. 2005, 127, 1638.
13. (a) Okamoto, T.; Kudoh, K.; Wakamiya, A.; Yamaguchi, S. Org. Lett. 2005, 7, 5301.
14. (b) Okamoto, T.; Kudoh, K.; Wakamiya, A.; Yamaguchi, S. Chem. Eur. J. 2007, 13, 548.
15. Mouri, K.; Wakamiya, A.; Yamada, H.; Kajiwara, T.; Yamaguchi, S. Org. Lett. 2007, 9, 93.
16. Fukazawa, A.; Yamada, H.; Yamaguch, S. Angew. Chem. Int. Ed. 2008, 47, 5582.
17. Fukazawa, A.; Hara, M.; Okamoto, T.; Son, E.-C.; Xu, C.; Tamao, K.; Yamaguchi, S. Org. Lett. 2008, 10, 913.
18. Zhang, H.; Karasawa, T.; Yamada, H.; Wakamiya, A.; Yamaguchi, S., unpublished results.
19. Sashida, H.; Yasuike, S. J. Heterocycl. Chem. 1998, 35, 725.
20. Takimiya, K.; Kunugi, Y.; Konda, Y.; Ebata, H.; Toyoshima, Y.; Otsubo, T. J. Am. Chem. Soc. 2006, 128, 3044.
21. Entwistle, C. D.; Batsanov, A. S.; Howard, J. A. K.; Fox, M. A.; Marder, T. B. Chem. Commun. 2004, 702.
22. Vagedes, D.; Kehr, G.; König, D.; Wedeking, K.; Fröhlich, R.; Erker, G.; Mück-Lichtenfeld, C.; Grimme, S. Eur. J. Inorg. Chem. 2002, 2015.
23. Crystallographic data for 4a and 4b have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC 706194 and 706195, respectively. Copies of the data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [fax: +44(1223)336033 or e-mail: data-request@ccdc.cam.ac.UK].
24. (a) Noda, T.; Shirota, Y. J. Am. Chem. Soc. 1998, 120, 9714.
25. (b) Noda, T.; Ogawa, H.; Shirota, Y. Adv. Mater. 1999, 11, 283.
26. Zaman, M. B.; Smith, M. D.; Ciurtin, D. M.; Loye, H.-C. Z. Inorg. Chem. 2002, 41, 4895.
27. Hiraoka, S.; Shiro, M.; Shionoya, M. J. Am. Chem. Soc. 2004, 126, 1214.
28. Wakamiya, A.; Mishima, K.; Ekawa, K.; Yamaguchi, S. Chem. Commun. 2008, 579.
29. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, J. A. Jr.; Vreven, T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; Pople, J. A. Gaussian 03 (revision C. 01); Gaussian, Inc.: Pittsburgh PA, 2004.