Palladium-catalyzed arylation of cyclopentadienes

Chemistry - A European Journal

Volumn 6, Issue 18, 2000, Pages 3426-3433

  Dyker, Gerald ^a   Heiermann, Jörg ^a   Miura, Masahiro ^b   Inoh, Jun Ichi ^b   Pivsa Art, Sommai ^b   Satoh, Tetsuya ^b   Nomura, Masakatsu ^b  

^a UNIVERSITY OF DUISBURG ESSEN   (Germany)

^b OSAKA UNIVERSITY   (Japan)

Author keywords

Domino reactions; Extended systems; Palladium catalysis; Rotamers

Indexed keywords

CYCLOPENTADIENE DERIVATIVE; PALLADIUM; UNCLASSIFIED DRUG; ZIRCONIUM DERIVATIVE; ZIRCONOCENE DICHLORIDE;

ARTICLE; CATALYSIS; ELECTRON TRANSPORT; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; SYNTHESIS;

EID: 0034665237     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/1521-3765(20000915)6:18<3426::AID-CHEM3426>3.0.CO;2-B     Document Type: Article

References (46)

1. M. S. Vollmer, F. Würthner, F. Effenberger, P. Emele, D. U. Meyer, T. Stümpfig, H. Port, H. C. Wolf, Chem. Eur. J. 1998, 4, 260-269, and references cited therein.
2. " Chemistry for the 21st Century" in Molecular Electronics (Eds.: J. Jortner, M. Ratner), Blackwell Science, Oxford, 1997.
3. Expanded, Contracted and Isomeric Porphyrins (Eds.: J. L. Sessler, S. J. Weghorn), Elsevier, 1997,.
4. a) C. Adachi, T. Tsuji, S. Saito, Appl. Phys. Lett. 1990, 56, 799-801;
5. b) Y. Ohmori, Y. Hironaka, M. Yoshida, N. Tada, A. Fujii, K. Yoshino, Synth. Metal 1997, 85, 1241-1242.
6. a) C. Janiak, H. Schumann, Adv. Organomet. Chem. 1991, 33, 291-393;
7. b) J. Okuda, Topics Curr. Chem. 1991, 160, 97-145;
8. c) D. Matt, M. Huhn, M. Bonnet, I. Tkatchenko, U. Englert, W. Kläui, Inorg. Chem. 1995, 34, 1288-1291;
9. d) S. Barry, A. Kucht, H. Kucht, M. D. Rausch, J. Organomet. Chem. 1995, 489, 195-199;
10. e) I. Kuksis, M. C. Baird, Organometallics 1996, 15, 4755-4762;
11. f) D. J. Hammack, M. M. Dillard, M. P. Castellani, A. L. Rheingold, A. L. Rieger, P. H. Rieger, Organometallics 1996, 15, 4791-4797;
12. g) I. Kuksis, I. Kovács, M. C. Baird, K. F. Preston, Organometallics 1996, 15, 4991-5002;
13. h) C. Janiak, R. Weimann, F. Görlitz, Organometallics 1997, 16, 4933-4936.
14. A. M. Bond, R. Colton, D. A. Fiedler, L. D. Field, D. Leslie, T. He, P. A. Humphery, C. M. Lindall, F. Marken, A. F. Masters, H. Schumann, K. Suehring, V. Tedesco, Organometallics 1997, 16, 2787-2797.
15. a) W. Broser, P. Siegle, H. Kurreck, Chem. Ber. 1968, 101, 69-83;
16. b) L. D. Field, K. M. Ho, C. M. Lindall, A. F. Masters, A. G. Webb, Aust. J. Chem. 1990, 43, 281-291;
17. c) T. R. Jack, C. J. May, J. Powell, J. Am. Chem. Soc. 1977, 99, 4707-4716;
18. d) H. Schumann, H. Kucht, A. Kucht, Z. Naturforsch. B 1992, 47, 1281-1289;
19. e) R. H. Lowack, K. P. C. Vollhardt, J. Organomet. Chem. 1994, 476, 25-32.
20. L. F. Tietze, U. Beifuss, Angew. Chem. 1993, 105, 137-170; Angew. Chem. Int. Ed. Engl. 1993, 32, 131-163.
21. L. F. Tietze, U. Beifuss, Angew. Chem. 1993, 105, 137-170; Angew. Chem. Int. Ed. Engl. 1993, 32, 131-163.
22. M. Miura, S. Pivsa-Art, G. Dyker, J. Heiermann, T. Satoh, M. Nomura, Chem. Commun. 1998, 1889-1890.
23. For a related reaction of iodocyclopentadienyl complexes with tributyl(cyclopentadienyl)stannane to give a mixture of 1,2,4,5-and 1,1,2,4-substituted cyclopentadienes, see: R. Boese, G. Bräunlich, J.-P. Gottenland, J.-T. Hwang, C. Troll, K. P. C. Vollhardt, Angew. Chem. 1996, 108, 1100-1102; Angew. Chem., Int. Ed. Engl. 1996, 35, 995-998.
24. For a related reaction of iodocyclopentadienyl complexes with tributyl(cyclopentadienyl)stannane to give a mixture of 1,2,4,5-and 1,1,2,4-substituted cyclopentadienes, see: R. Boese, G. Bräunlich, J.-P. Gottenland, J.-T. Hwang, C. Troll, K. P. C. Vollhardt, Angew. Chem. 1996, 108, 1100-1102; Angew. Chem., Int. Ed. Engl. 1996, 35, 995-998.
25. G. Dyker, J. Org. Chem. 1993, 58, 234-238.
26. W. A. Herrmann, C. Brossmer, C.-P. Reisinger, T. H. Riermeier, K. Öffele, M. Beller, Chem. Eur. J. 1997, 3, 1357-1364, and references cited therein.
27. For a review on sterically hindered phosphines, see: V. V. Grushin, H. Alper, Chem. Rev. 1994, 94, 1047-1062, and references cited therein.
28. The use of tert-butylphosphine in other palladium-catalyzed reactions of aryl bromides and chlorides: animation a) M. Nishiyama, T. Yamamoto, Y. Koie, Tetrahedron Lett. 1998, 39, 617-620;
29. b) T. Yamamoto, M. Nishiyama, Y. Koie, Tetrahedron Lett. 1998, 39, 2367-2370; Suzuki coupling:
30. c) A. F. Littke, G. C. Fu., Angew. Chem. 1998, 110, 3586-3587; Angew. Chem. Int. Ed. Engl., 1998, 37, 3387-3388; Heck reaction:
31. c) A. F. Littke, G. C. Fu., Angew. Chem. 1998, 110, 3586-3587; Angew. Chem. Int. Ed. Engl., 1998, 37, 3387-3388; Heck reaction:
32. d) A. F. Littke, G. C. Fu., J. Org. Chem. 1999, 64, 10-11; aryloxylation:
33. e) G. Mann, C. Incarvito, A. L. Rheingold, J. F. Hartwig, J. Am. Chem. Soc. 1999, 121, 3224-3225.
34. R. Willem, A. Jans, C. Hoogzand, M. Gielen, G. V. Binst, H. Pepermans, J. Am. Chem. Soc. 1985, 107, 28-32.
35. a) H. Horino, M. Arai, N. Inoue, Bull. Chem. Soc. Jpn. 1974, 47, 1683-1686;
36. b) R. F. Heck, J. Am. Chem. Soc. 1968, 90, 5518-5526.
37. a) O. Reiser, M. Weber, A. de Meijere, Angew. Chem. 1989, 101, 1071-1072; Angew. Chem. Int. Ed. Engl. 1989, 28, 1037-1038;
38. a) O. Reiser, M. Weber, A. de Meijere, Angew. Chem. 1989, 101, 1071-1072; Angew. Chem. Int. Ed. Engl. 1989, 28, 1037-1038;
39. b) M. Weber, Ph.D. Dissertation, Hamburg, 1992.
40. F. G. Bordwell, Acc. Chem. Res. 1988, 21, 456-463.
41. For exchange of cyclopentadienyl ligands, see: Comprehensive Organometallic Chemistry, Vol. 8 (Eds.: G. Wilkinson, F. G. A. Stone, E. W. Abel), Pergamon, Oxford, 1982, p. 1048.
42. K. Sekiguchi, A. Sera, Y. Orsuki, K. Maruyama, Bull. Chem. Soc. Jpn. 1975, 48, 4090-4094.
43. B. H. Freeman, J. M. F. Gagan, D. Lloyd, Tetrahedron 1973, 29, 4307-4312.
44. S. S. Hirsch, W. J. Bailey, J. Org. Chem. 1978, 43, 4090-4094.
45. A. Jutand, A. Mosleh, J. Org. Chem. 1997, 62, 261-274.
46. C. F. Koelsch, P. R. Johnson, J. Am. Chem. Soc. 1943, 65, 567-573.