Palladium-Catalyzed Arylation of Ketone Enolates: An Expeditious Entry to Tamoxifen-Related 1,2,2-Triarylethanones

Organic Letters

Volumn 4, Issue 9, 2002, Pages 1591-1594

  Churruca, Fátima ^a   SanMartin, Raul ^a   Tellitu, Imanol ^a   Dominguez, Esther ^a  

^a UNIVERSITY OF THE BASQUE COUNTRY UPV EHU   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ANTINEOPLASTIC HORMONE AGONISTS AND ANTAGONISTS; DRUG DERIVATIVE; DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; KETONE; PALLADIUM; TAMOXIFEN;

ALKYLATION; ARTICLE; CATALYSIS; CHEMISTRY; SYNTHESIS;

ALKYLATION; ANTINEOPLASTIC AGENTS, HORMONAL; CATALYSIS; INDICATORS AND REAGENTS; KETONES; PALLADIUM; TAMOXIFEN;

EID: 0037007736     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol025811h     Document Type: Article

References (44)

1. (a) Olivera, R.; Pascual, S.; Herrero, M.; SanMartin, R.; Domínguez, E. Tetrahedron Lett. 1999, 40, 3479-3480.
2. (b) Olivera, R.; SanMartin, R.; Domínguez, E. J. Org. Chem. 2000, 65, 7010-7019 and references therein.
3. (a) After searching the literature, only one report of a related dibenzo-[a,c]phenanthridine was found. See: Kiselyov, A. S. Tetrahedron Lett. 1995, 36, 493-496. For recent reports on the biological properties of benzo[c]-phenanthridines, see:
4. (b) Asano, Y.; Yamashita, M.; Nagai, K.; Kuriyama, M.; Yamada, K.; Tomioka, K. Tetrahedron Lett. 2001, 42, 8493-8495.
5. Salmore, A. K.; Hunter, M. D. J. Chem. Ecol. 2001, 27, 1713-1727.
6. (d) Ito, C.; Itoigawa, M.; Tokuda, H.; Kuchide, M.; Nishino, H.; Furukawa, H. Planta Med. 2001, 67, 473-475.
7. (e) Slaninova, I.; Taborska, E.; Bochorakova, H.; Slanina, J. Cell Biol. Toxicol. 2001, 17, 51-63.
8. (f) Harayama, T.; Akiyama, T.; Akamatsu, H.; Kawano, K.; Abe, H.; Takeuchi, Y. Synhesis 2001, 444-450.
9. (g) Harayama, T.; Akiyama, T.; Nakano, Y.; Shibaike, K.; Akamatsu, H.; Hori, A.; Abe, H.; Takeuchi, Y. Synthesis 2002,
10. The synthesis and biological effect of tamoxifen and its analogues have attracted much attention. See: (a) Delcey, C. D.; Huel, C.; Bisagnani, E. Heterocycles 1995, 41, 1721-1730.
11. (b) Lashley, M. R.; Nantz, M. H. Tetrahedron Lett. 2000, 41, 3295-3298 and references therein.
12. Valliant, J. F.; Paul Schaffer, P.; Stephenson, K. A.; Britten, J. F. J. Org. Chem. 2002, 67, 383-387.
13. (a) Al-Maharik, N. I.; Kaltia, Seppo, A. A.; Mutikainen, I.; Waehaelae, K. J. Org. Chem. 2000, 65, 2305-2308.
14. (b) SanMartin, R.; Martínez de Marigorta, E.; Domínguez, E. Tetrahedron 1994, 50, 2255-2264. Other complementary procedures that allow a wider range of substitution paterns are described in:
15. Olivera, R.; SanMartin, R.; Domínguez, E. Solans, X.; Urtiaga, M. K.; Arriortua, M. I. J. Org. Chem. 2000, 65, 6398-6411 and references therein.
16. (a) Piers, E.; Oballa, R. M. tetrahedron Lett. 1995, 36, 5837-5860.
17. (b) Ryan, J. H.; Stang, P. J. Tetrahedron Lett. 1997, 38, 5061-5064.
18. Muratake, H.; Hayakawa, A.; Natsume, M. Chem. Pharm Bull. 2000, 48, 1558-1566.
19. (d) Fox, J. M.; Huang, X.; Chieffi, A.; Buchwald, S. L. J. Am. Chem. Soc. 2000, 122, 1360-1370 and references included therein.
20. (e) Deng, H. B.; Konopelski, J. P. Org. Lett. 2001, 3, 3001-3004.
21. (a) Beugelmans, R.; Boudet, B.; Quintero, L. Tetrahedron Lett. 1980, 21, 1943-1944.
22. (b) Kessar, S. V. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Semmelhack, M. F., Eds.; Pergamon Press: New York, 1991; Vol. 4, Chapter 2.3.
23. Pinhey, J. T. Pure Appl. Chem. 1996, 68, 819-824.
24. (d) Mino, T.; Matsuda, T.; Maruhashi, K.; Yamashita, M. Organometallics 1997, 16, 3241-3242.
25. (a) Palucki, M.; Buchwald, S. L. J. Am. Chem. Soc. 1997, 119, 11108-11109.
26. (b) Hamann, B. C.; Hartwig, J. F. J. Am. Chem. Soc. 1997, 119, 12382-12383.
27. Kawatsura, M.; Hartwig, J. F. J. Am. Chem. Soc. 1999, 121, 1473-1478
28. (d) Satoh, T.; Kametani, Y.; Terao, Y.; Miura, M.; Nomura, M. Tetrahedron Lett. 1999, 40, 5345-5348.
29. (e) Terao, Y.; Kametani, Y.; Wakui, H.; Satoh, T.; Miura, M.; Nomura, M. Tetrahedron, 2001, 57, 5967-5974.
30. (f) Mutter, R.; Campbell, I. B.; Martin de la Neva, E, V.; Merritt, A. T.; Wills, M. J. Org. Chem, 2001, 66, 3284-3290.
31. (g) Solé D.; Vallverdú, L.; Peidró, E.; Bonjoch, J. Chem. Commun. 2001, 1888-1889.
32. (h) Hamada, T.; Chieffi, A.; Åhman, J.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 1261-1268.
33. (a) Mutter, R.; Martin de la Neva, E, V.; Wills, M. Chem. Commun. 2000, 1675-1676. See also:
34. (b) Shaughnessy, K. H.; Hamann, B. C.; Hartwig, J. F. J. Org. Chem. 1998, 63, 6546-6553.
35. Satoh, T.; Inoh, J.-I.; Kawamura, Y.; Kawamura, Y.; Kametani, Y.; Miura, M.; Nomura, M. Bull. Chem. Soc. Jpn. 1998, 71, 2239-2246.
36. 4Cl (5 x 100 mL), dried over anhydrous sodium sulfate, and evaporated in vacuo to give a residue that was purified by flash chromatography on silicagel using 10-50% EtOAc/hexane as eluent.
37. (a) Moradi, W. A.; Buchwald, S. L. J. Am. Chem. Soc. 2001, 123, 7996-8002.
38. (b) Lee, S.; Beare, N. A.; Hartwig, J. F. J. Am. Chem. Soc. 2001, 123, 8410-8411.
39. Useful insights into the mechanism of the Pd-catalyzed arylation of enolates and other related cross-coupling reactions can be found in: (a) Culkin, D. A.; Hartwig, J. F. J. Am. Chem. Soc. 2001, 123, 5816-5817.
40. (b) Amatore, C.; Jutand, A. Ace. Chem. Res. 2000, 33, 314-321. See also refs 7a and 7d.
41. Nilsson, P.; Larhed, M.; Hallberg, A. J. Am. Chem. Soc. 2001, 123, 8217-8225.
42. (a) Old, D. W.; Wolfe, J. P., Buchwald, S. L. J. Am. Chem. Soc. 1998, 120, 9722-9723.
43. (b) Ȧhman, J.; Wolfe, J. P.; Trotman, M. V.; Palucki, M.; Buchwald, S. L. J. Am. Chem. Soc. 1998, 120, 1918-1919.
44. For previous reports on one-pot α,α-diarylation reactions of ketones see refs 5d, 7a, 7c,d, and 14a. Similar diarylations of other carbonylic compounds have been reported in refs 8b and 11a.