Highly stereoselective synthesis, structure, and application of (E)-9-[2-(Silyl)ethenyl]-9H-carbazoles

Journal of Organic Chemistry

Volumn 70, Issue 21, 2005, Pages 8550-8555

  Marciniec, Bogdan ^a   Majchrzak, Mariusz ^a   Prukała, Wiesław ^a   Kubicki, Maciej ^a   Chadyniak, Dariusz ^a  

^a ADAM MICKIEWICZ UNIVERSITY   (Poland)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; DERIVATIVES; IODINE COMPOUNDS; SILANES; STEREOCHEMISTRY; SUBSTITUTION REACTIONS;

HIYAMA COUPLING; IODOBENZENE; SILYLATIVE COUPLING; STEREOSELECTIVE SYNTHESIS;

SYNTHESIS (CHEMICAL);

9 [2 (SILYL)ETHENYL] 9H CARBAZOLE DERIVATIVE; CARBAZOLE DERIVATIVE; IODOBENZENE; N (PHENYLVINYL)CARBAZOLE; N (TRIETHOXYSILYL)VINYLCARBAZOLE; N VINYLCARBAZOLE DERIVATIVE; PALLADIUM; RUTHENIUM DERIVATIVE; SILANE DERIVATIVE; SILYLVINYLCARBAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; REACTION ANALYSIS; SILYLATION; STEREOCHEMISTRY; STRUCTURE ANALYSIS; SYNTHESIS; X RAY ANALYSIS;

EID: 26844573776     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo051629t     Document Type: Article

References (30)

1. Colvin, E. W. Silicon Reagents in Organic Synthesis; Academic Press: London, 1988.
2. Oshima, K. In Science of Synthesis; Fleming, I., Ed.; G. Thieme: Stuttgart, 2002; Vol. 2, p 685.
3. The Chemistry of Organosilicon Compounds; Patai, S., Rappaport, Z., Eds.; Wiley: Chichester, 1998; Chapter 3.
4. Denmark S. E.; Ober M. H. Aldrichimica Acta 2003, 36, 75-85.
5. Hiyama, T. J. Organomet. Chem. 2002, 653, 58.
6. (b) Hiyama, T.; Hatanaka, Y. Pure Appl. Chem. 1994, 66, 1471.
7. (c) Hiyama, T. In Metal-catalyzed, Cross-coupling Reactions; Diederich, F., Stang, P. J., Eds.; Wiley-VCH: Weinheim, Germany, 1998; Chapter 10.
8. Marciniec, B.; Zaidlewicz, M.; Pietraszuk, C.; Kownacki, I. In Comprehensive Organic Functional Group Transformations II; Katritzky, A. R., Taylor, R. J. K., Eds.; Elsevier Science: Amsterdam, 2005; Charter 2.18.
9. (a) Marciniec, B.; Pietraszuk, C. Curr. Org. Chem. 2003, 7, 691-735.
10. (b) Marciniec, B.; Pietraszuk, C. In Handbook of Metathesis; Grubbs, R. H., Ed.; Wiley-VCH: Wenheim, 2003; Vol. 2, Chapter 13.
11. (c) Marciniec, B.; Pietraszuk, C. In Topics in Organometallic Chemistry; Bruneau, C., Dixneuf, P. H., Eds.; Springer-Verlag: Berlin, Heidelberg, New York, 2004; pp 197-248.
12. (a) Wakatsuki, Y.; Yamazaki, H.; Nakano, M.; Yamamoto; Y. J. Chem. Soc., Chem. Commun. 1991, 703-704.
13. (b) Marciniec, B.; Pietraszuk; C. J. Chem. Soc., Chem. Commun. 1995, 2003-2004.
14. (c) Marciniec, B.; Pietraszuk, C. Organometallics 1997, 16, 4320-4326.
15. (a) Marciniec, B.; Kujawa, M.; Pietraszuk, C. Organometallics 2000, 19, 1677-1681.
16. (b) Marciniec, B.; Chadyniak, D.; Krompiec, S. Tetrahedron Lett. 2004, 45, 4065-4068.
17. (c) Jankowska, M.; Marciniec, B.; Pietraszuk, C.; Cytarska, J.; Zaidlewicz, M. Tetrahedron Lett. 2004, 45, 6615-6618.
18. (d) Itami, Y.; Marciniec, B.; Kubicki, M. Organometallics, 2003, 22, 3717-3722.
19. (e) Itami, Y.; Marciniec, B.; Kubicki, M. Chem. Eur. J. 2004, 10, 1239-1248.
20. (f) Pawluc, P.; Marciniec, B.; Hreczycho, G.; Gaczewska, B.; Itami, Y. J. Org. Chem. 2005, 70, 370-372.
21. (g) Pawluc, P.; Hreczycho, G.; Marciniec, B. Synlett 2005, 7, 1105-1108.
22. (h) Marciniec, B.; Majchrzak, M.; Prukała, W.; Chadyniak, D. Polish Patent P-368097, 2004.
23. Allen, F. H. Acta Crystalogr. Part B, 2002, 58, 380.
24. Tsutsui, K.; Hirotsu, K.; Umesaki, M.; Kurahashi, M.; Shimada, A.; Higuchi, T. Acta Crystalogr., Sect. B 1976, 32, 3049.
25. Sheldrick, G. M. Acta Crystallogr., Sect. A 1990, 46, 467-473.
26. (a) Yi C. S.; Lee D. W.; Chen, Y. Organometallics 1999, 18, 2043.
27. (b) Ukai, T.; Kawazura, H.; Ishii, Y. J. Organomet. Chem. 1974, 65, 253.
28. KUMA KM4 User's Guide, Version 5.0; KUMA Diffraction: Wroclaw, Poland, 1991.
29. Sheldrick, G. M. SHELXL-97, Program for the Refinement of Crystal Structures; University of Göttingen, Göttingen (Germany), 1997.
30. Sterechemical Workstation; Siemens Analytical X-ray Instruments Inc., Madison, WI, 1989.