Efficient preparation of 2-azulenylboronate and Miyaura-Suzuki cross-coupling reaction with aryl bromides for easy access to poly(2-azulenyl)benzenes

Tetrahedron

Volumn 60, Issue 25, 2004, Pages 5357-5366

  Ito, Shunji ^a   Terazono, Tomomi ^b   Kubo, Takahiro ^b   Okujima, Tetsuo ^b   Morita, Noboru ^b   Murafuji, Toshihiro ^c   Sugihara, Yoshikazu ^c   Fujimori, Kunihide ^d   Kawakami, Jun ^a   Tajiri, Akio ^a  

^a HIROSAKI UNIVERSITY   (Japan)

^b TOHOKU UNIVERSITY   (Japan)

^c YAMAGUCHI UNIVERSITY   (Japan)

^d SHINSHU UNIVERSITY   (Japan)

Author keywords

Azulenylboronate; Miyaura Suzuki cross coupling; Palladium catalyzed reaction; Redox property; Violene cyanine hybrid

Indexed keywords

1,2 BIS(2 AZULENYL)BENZENE; 1,2,4 TRIS(2 AZULENYL)BENZENE; 1,3,5 TRIS(2 AZULENYL)BENZENE; 2 AZULENYLBORONATE; 2 ISOPROPOXY 4,4,5,5 TETRAMETHYL 1,3,2 DIOXABOROLANE; BENZENE DERIVATIVE; BORONIC ACID DERIVATIVE; BROMINE DERIVATIVE; DIOXANE DERIVATIVE; ORGANIC SOLVENT; PALLADIUM; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CATALYST; CROSS COUPLING REACTION; CYCLIC POTENTIOMETRY; OXIDATION REDUCTION REACTION; PRIORITY JOURNAL; SUZUKI REACTION;

LATEOLABRAX JAPONICUS;

EID: 2542498735     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2004.04.057     Document Type: Article

References (47)

1. See e.g.: (a) Billington D.C. Trost B.M., Fleming I. Comprehensive Organic Synthesis. Vol. 3:1991;Pergamon, Oxford. Chapter 2.1
2. Tamao K. Trost B.M., Fleming I. Comprehensive Organic Synthesis. Vol. 3:1991;Pergamon, Oxford. Chapter 2.2
3. Knight D.W. Trost B.M., Fleming I. Comprehensive Organic Synthesis. Vol. 3:1991;Pergamon, Oxford. Chapter 2.3
4. Sonogashira K. Trost B.M., Fleming I. Comprehensive Organic Synthesis. Vol. 3:1991;Pergamon, Oxford. Chapter 2.4
5. Horino H., Asao T., Inoue N. Bull. Chem. Soc. Jpn. 64:1991;183-190
6. Dyker G., Borowski S., Heiermann J., Körning J., Opwis K., Henkel G., Köckerling M. J. Organomet. Chem. 606:2000;108-111
7. Balschukat D., Dehmlow E.V. Chem. Ber. 119:1986;2272-2288
8. (c) Otani, H.; Tsunoda, Y. Presented at 79th CSJ National Meeting, Kobe, March 31, 2001, Abstr., No. 4B2 10.
9. Ito S., Inabe H., Okujima T., Morita N., Watanabe M., Imafuku K. Tetrahedron Lett. 41:2000;8343-8347
10. Fabin K.H.H., Elwahy A.H.M., Hafner K. Tetrahedron Lett. 41:2000;2855-2858
11. Kane J.L., Shea K.M., Crombie A.L., Danheiser R.L. Org. Lett. 3:2001;1081-1084
12. Okujima T., Ito S., Morita N. Tetrahedron Lett. 43:2002;1261-1264
13. Ito S., Okujima T., Morita N. J. Chem. Soc., Perkin Trans. 1. 2002;1896-1905
14. Fujita M., Oka H., Ogura K. Tetrahedron Lett. 36:1995;5247-5250
15. See e.g.: (a) Miyaura N., Suzuki A. Chem. Rev. 95:1995;2457-2483
16. Suzuki A. J. Organomet. Chem. 576:1999;147-168
17. Suzuki A. Diederich F., Stang P.J. Metal-Catalyzed Cross-Coupling Reactions. 1998;49-97 Wiley-VCH, Weinheim
18. Pelter A., Smith K., Brown H.C. Borane Reagents. 1988;Academic, London
19. For reviews: (a) Ishiyama T., Miyaura N. J. Syn. Org. Chem. 57:1999;503-511
20. Ishiyama T., Miyaura N. J. Organomet. Chem. 611:2000;392-402
21. Murata M., Watanabe S., Masuda Y. J. Org. Chem. 62:1997;6458-6459
22. Murata M., Oyama T., Watanabe S., Masuda Y. J. Org. Chem. 65:2000;164-168
23. Kurotobi K., Tabata H., Miyauchi M., Murafuji T., Sugihara Y. Synthesis. 2002;1013-1016
24. Kurotobi K., Miyauchi M., Takakura K., Murafuji T., Sugihara Y. Eur. J. Org. Chem. 2003;3663-3665
25. Hünig S., Kemmer M., Wenner H., Perepichka I.F., Bäuerle P., Emge A., Gescheid G. Chem. Eur. J. 5:1999;1969-1973
26. Hünig S., Kemmer M., Wenner H., Barbosa F., Gescheidt G., Perepichka I.F., Bäuerle P., Emge A., Peters K. Chem. Eur. J. 6:2000;2618-2632
27. Hünig S., Perepichka I.F., Kemmer M., Wenner H., Bäuerle P., Emge A. Tetrahedron. 56:2000;4203-4211
28. Hünig S., Langels A., Schmittel M., Wenner H., Perepichka I.F., Peters K. Eur. J. Org. Chem. 2001;1393-1399
29. Ito S., Inabe H., Okujima T., Morita N., Watanabe M., Harada N., Imafuku K. Tetrahedron Lett. 42:2001;1085-1089
30. Ito S., Inabe H., Okujima T., Morita N., Watanabe M., Harada N., Imafuku K. J. Org. Chem. 66:2001;7090-7101
31. McDonald R.N., Richmond J.M., Curtis J.R., Petty H.E., Hoskins T.L. J. Org. Chem. 41:1976;1811-1821
32. Ito S., Nomura A., Morita N., Kabuto C., Kobayashi H., Maejima S., Fujimori K., Yasunami M. J. Org. Chem. 67:2002;7295-7302
33. Vaultier M., Carboni B. Abel E.W., Stone F.G.A., Wilkinson G. Comprehensive Organometallic Chemistry II. Vol. 11:1995;191-276 Pergamon, Oxford
34. Miyaura N., Maruoka K. Komiya S. Synthesis of Organometallic Compounds. 1997;345-390 Wiley, New York
35. Zeller K.-P. 4th ed. Houben-Weyl; Methoden der Organischen Chemie. Vol. V:1985;Georg Thieme, Stuttgart. Part 2C, pp 127-418
36. Ito S., Kubo T., Morita N., Matsui Y., Watanabe T., Ohta A., Fujimori K., Murafuji T., Sugihara Y., Tajiri A. Tetrahedron Lett. 45:2004;2891-2894
37. Kurotobi K., Tabata H., Miyauchi M., Mustafizur A.F.M.R., Migita K., Murafuji T., Sugihara Y., Shimoyama H., Fujimori K. Synthesis. 2003;30-34
38. Andersen M.W., Hildebrandt B., Köster G., Hoffmann R.W. Chem. Ber. 122:1989;1777-1782
39. Mohanakrishnan A.K., Lakshmikantham M.V., McDougal C., Cava M.P., Baldwin J.W., Metzger R.M. J. Org. Chem. 63:1998;3105-3112
40. 18a.
41. Nefedov V.A., German N.A., Lutsenko A.I., Nikishin G.I. J. Org. Chem. U.S.S.R. 23:1987;154-162
42. Plattner P.A., Sandrin R., Wyss J. Helv. Chim. Acta. 29:1946;1604-1608
43. Morita T., Abe N., Takase K. J. Chem. Soc., Perkin Trans. 1. 2000;3063-3070
44. O'Keeefe D.F., Dannock M.C., Marcuccio S.M. Tetrahedron Lett. 33:1992;6679-6680
45. Wright S.W., Hageman D.L., McClure L.D. J. Org. Chem. 59:1994;6095-6097
46. Moreno-Mañas M., Pérez M., Pleixats R. J. Org. Chem. 61:1996;2346-2351
47. Smith K.A., Campi E.M., Jackson W.R., Maruccio S., Naeslund C.G.M., Deacon G.B. Synlett. 1997;131-132