Synthesis of symmetrical and unsymmetrical 9,10-diarylanthracene derivatives via bis-Suzuki-Miyaura cross-coupling reaction

Synthesis

Volumn , Issue 4, 2004, Pages 549-557

  Kotha, Sambasivarao ^a   Ghosh, Arun Kumar ^a   Deodhar, Kodand Dinkar ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY BOMBAY   (India)

Author keywords

Arenes; Boron; Coupling; Palladium; Polymers

Indexed keywords

CATALYSIS; DENDRIMERS; DERIVATIVES; SYNTHESIS (CHEMICAL); TRANSITION METALS;

CROSS-COUPLING REACTIONS; THIOPENE;

AROMATIC COMPOUNDS;

ANTHRACENE DERIVATIVE; DENDRIMER; METAL; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; POLYMER; THIOPHENE DERIVATIVE;

ARTICLE; ASYMMETRIC SYNTHESIS; CATALYSIS; CHEMICAL STRUCTURE; QUANTUM YIELD; REACTION ANALYSIS; SUZUKI REACTION;

EID: 1642338455     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2004-815981     Document Type: Article

References (56)

1. Marcus, R. A. Angew. Chem., Int. Ed. Engl. 1993, 32, 1111.
2. Paddon-Row, M. N. Acc. Chem. Res. 1994, 27, 18.
3. Huber, R. Angew. Chem., Int. Ed. Engl. 1989, 28, 848.
4. Deisenhofer, J.; Michel, H. Angew. Chem., Int. Ed. Engl. 1989, 28, 829.
5. Williams, D. J. Angew. Chem., Int. Ed. Engl. 1984, 23, 690.
6. Kanis, D. R.; Ratner, M. A.; Mark, T. J. J. Am. Chem. Soc. 1992, 114, 10338.
7. Kaino, T.; Tomaru, S. Adv. Mater. 1993, 5, 172.
8. Grätzel, M.; Kalyanasundaram, K. Curr. Sci. 1994, 66, 706.
9. Babu, K. S. C.; Srivasta, O. N.; Rao, G. V. S. Curr. Sci. 1994, 66, 715.
10. Nalwa, H. S.; Kakuta, A. Appl. Organomet. Chem. 1992, 6, 645.
11. Wagner, G.; Herrmann, R.; Scherer, W. J. Organomet. Chem. 1996, 516, 225.
12. Yee, W. A.; Kuzmin, V. A.; Kliger, D. S.; Hammond, G. S.; Twarowski, A. J. J. Am. Chem. Soc. 1979, 707, 5104.
13. Liu, D. K. K.; Faulkner, L. R. J. Am. Chem. Soc. 1977, 99, 4594.
14. Wilson, T. J. Am. Chem. Soc. 1969, 91, 2387.
15. Engstrom, R. C.; Johnson, K. W.; Desjarlais, S. Anal. Chem. 1987, 59, 670.
16. Molay, J. T.; Bard, A. J. J. Am. Chem. Soc. 1971, 93, 5968.
17. Maricle, D. L.; Maurer, A. J. Am. Chem. Soc. 1967, 89, 188.
18. Adam, W.; Cueto, O.; Yany, F. J. Am. Chem. Soc. 1978, 700, 2587.
19. Adam, W.; Cancio, E. M.; Rodriguez, O. Photochem. Photobiol. 1978, 27, 617.
20. Romanets, R. G.; Prock, A.; Zahradnik, R. J. Phys. Chem. 1970, 53, 4093.
21. Herkstroeter, W. G.; Merkel, P. B. J. Photochem. 1981, 16, 331.
22. (a) Smet, M.; Dijk, J. V.; Dehanen, W. Synlett 1999, 495.
23. (b) Smet, M.; Dijk, J. V.; Dehanen, W. Tetrahedron 1999, 55, 7859; and references cited therein.
24. Kotha, S.; Ghosh, A. K.; Behera, M. Indian J. Chem., Sect. B 2002, 47, 2330.
25. Ingold, K. C.; Marshall, G. P. J. Chem, Soc. 1926, 3080.
26. Willmart, A. Bull. Soc. Chim. Fr. 1942, 9, 83.
27. Etienne, A.; Arditti, G.; Chmelevsky, A. Bull. Soc. Chim. Fr. 1965, 669.
28. Blank, D. H.; Gribble, G. W. Tetrahedron Lett. 1997, 38, 4761.
29. Kauffman, J. M. Synthesis 2001, 197.
30. Goossens, R.; Smet, M.; Dehanen, W. Tetrahedron Lett. 2002, 43, 6605.
31. Zeng, B.-b.; King, S. B. Synthesis 2002, 2335.
32. Pai, J.; Yu, W.-L.; Ni, J.; Lai, Y.-H.; Huang, W.; Heerger, A. J. Macromolecules 2001, 34, 7241.
33. Gigli, A. W.; Barbarella, G.; Favaretto, L.; Cacialli, F.; Cingolani, R. Appl. Phys. Lett. 1999, 75, 439.
34. Granlund, T.; Theander, M.; Bergreen, M.; Anderson, M. R.; Ruzeckas, A.; Sundstrom, V.; Bjork, G.; Granstrom, M.; Inganas, O. Chem. Phys. Lett. 1998, 288, 879.
35. van Mullekom, H. A. M. Ph.D. Thesis; Endhoven University of Technology: The Netherlands, 2000.
36. Cooke, A.; Wagener, K. B. Macromolecules 1991, 26, 2704.
37. Iwatsuki, S.; Kubo, M.; Ito, Y. Chem. Lett. 1993, 1085.
38. Cornelissen, J. J. L. M.; Peeters, E.; Jansen, R. J.; Meijer, E. W. Acta Polym. 1998, 49, 476.
39. Kim, K.-K.; Son, S.-H.; Yoon, S.-H.; Bae, J.-S.; Lee, Y.-G.; Im, S.-G.; Kim, J.-E.; Lee, J.-C. WO 2002O88274, 2002; Chem. Abstr. 2002, 137, 360139.
40. Azuma, H.; Hosokawa, C.; Kusumoto, T. Japanese Patent 200053676, 2000; Chem. Abstr. 2000, 132, 173450.
41. Miyaura, N.; Yanagi, T.; Suzuki, A. Synth. Commun. 1981, 513.
42. Martin, A. R.; Yang, Y. Acta. Chem. Scand. 1993, 47, 221.
43. (a) Suzuki, A. Pure Appl. Chem. 1994, 66, 213.
44. (b) Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457.
45. (a) Tanaka, K.; Endo, K.; Aoyama, Y. Chem. Lett. 1999, 887.
46. (b) Brownstein, S. K.; Ding, J.; Robertson, G.; Roovers, J. J. Org. Chem. 2002, 67, 663.
47. Stanforth, S. P. Tetrahedron 1998, 54, 263.
48. Suzuki, A. J. Organomet. Chem. 1999, 576, 147.
49. Kotha, S.; Lahiri, K.; Kasinath, D. Tetrahedron 2002, 58, 9633.
50. Kotha, S.; Ghosh, A. K. Synlett 2002, 451.
51. Balaganesan, B.; Sen, W. J.; Chen, C. H. Tetrahedron Lett. 2003, 44, 5747.
52. Jones, S. J.; Atherton, C. C. Synth. Commun. 2001, 31, 1799.
53. Aldrich Handbook of Fine Chemicals and Laboratory Equipment 2003-2004; Aldrich: Milwaukee, 2003, Cat. No. 26930-1, 230.
54. (a) Coulson, D. R. Inorg. Synth. 1972, 13, 121.
55. (b) Brandsma, L.; Vasilevsky, S. F.; Verkruijsse, H. S. Application of Transition Metal Catalyst in Organic Synthesis; Springer: Berlin, 1998, 13.
56. Teki, Y.; Miyamoto, S.; Nakatsuji, M.; Miura, Y. J. Am. Chem. Soc. 2001, 123, 294.