Palladium-catalyzed benzylic arylation of N-benzylxanthone imine

Organic Letters

Volumn 10, Issue 20, 2008, Pages 4689-4691

  Niwa, Takashi ^a   Yorimitsu, Hideki ^a   Oshima, Koichiro ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 59249098736     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol802070d     Document Type: Article

References (32)

1. α-Arylation of carbonyls: (a) Culkin, D. A.; Hartwig, J. F. Acc. Chem. Res. 2003, 36, 234-245.
2. (b) Hamann, B. C.; Hartwig, J. F. J. Am. Chem. Soc. 1997, 119, 12382-12383.
3. (c) Palucki, M.; Buchwald, S. L. J. Am. Chem. Soc. 1997, 119, 11108-11109.
4. (d) Gaertzen, O.; Buchwald, S. L. J. Org. Chem. 2002, 67, 465-475.
5. (e) Satoh, T.; Inoh, J.; Kawamura, Y.; Kawamura, Y.; Miura, M.; Nomura, M. Bull Chem. Soc. Jpn. 1998, 71, 2239-2246. γ-Arylations of α,β-unsaturated carbonyl compounds:
6. (f) Terao, Y.; Satoh, T.; Miura, M.; Nomura, M. Tetrahedron Lett. 1998, 39, 6203-6206.
7. (g) Muratake, H.; Natsume, M. Tetrahedron Lett. 1997, 38, 7581-7582.
8. Intermolecular arylation at the activated benzylic or allylic positions: (a) Inoh, J.; Satoh, T.; Pivsa-Art, S.; Miura, M.; Nomura, M. Tetrahedron Lett. 1998, 39, 4673-4676.
9. (b) Dyker, G.; Heiermann, J.; Miura, M.; Inoh, J.; Pivsa-Art, S.; Satoh, T.; Nomura, M. Chem. Eur. J. 2000, 6, 3426-3433.
10. (c) Dyker, G.; Heiermann, J.; Miura, M. Adv. Synth. Catal. 2003, 345, 1127-1132.
11. (d) Niwa, T.; Yorimitsu, H.; Oshima, K. Org. Lett. 2007, 9, 2373-2375.
12. (e) Mousseau, J. J.; Larivée, A.; Charette, A. B. Org. Lett. 2008, 10, 1641-1643.
13. (f) Campeau, L.-C.; Schipper, D. J.; Fagnou, K. J. Am. Chem. Soc. 2008, 130, 3266-3267.
14. Intramolecular arylative cyclization at the benzylic positions: (a) Ren, H.; Knochel, P. Angew. Chem., Int. Ed. 2006, 45, 3462-3465.
15. (b) Ren, H.; Li, Z.; Knochel, P. Chem. Asian J. 2007, 2, 416-433.
16. (c) Dong, C.-G.; Hu, Q.-S. Angew. Chem., Int. Ed. 2006, 45, 2289-2292.
17. (d) Hu, Q.-S. Synlett 2007, 1331-1345.
18. (e) Catellani, M.; Motti, E.; Ghelli, S. Chem. Commun. 2000, 2003-2004.
19. (f) Salcedo, A.; Neuville, L.; Zhu, J. J. Org. Chem. 2008, 73, 3600-3603.
20. Arylation of N-tert-butymydrazones as an acyl anion equivalent: Takemiya, A.; Hartwig, J. F. J. Am. Chem. Soc. 2006, 128, 14800-14801.
21. 3)-H arylation involving cleavage of less acidic hydrogens: (a) Zaitsev, V. G.; Shabashov, D.; Daugulis, O. J. Am. Chem. Soc. 2005, 127, 13154-13155.
22. (b) Shabashov, D.; Daugulis, O. Org. Lett. 2005, 7, 3657-3659.
23. (c) Reddy, B. V. S.; Reddy, L. R.; Corey, E. J. Org. Lett. 2006, 8, 3391-3394.
24. (d) Kalyani, D.; Deprez, N. R.; Desai, L. V.; Sanford, M. S. J. Am. Chem. Soc. 2005, 127, 7330-7331.
25. (e) Giri, R.; Maugel, N.; Li, J.-J.; Wang, D.-H.; Breazzano, S. P.; Saunders, L. B.; Yu, J.-Q. J. Am. Chem. Soc. 2007, 129, 3510-3511.
26. (f) Barder, T. E.; Walker, S. D.; Martinelli, J. R.; Buchwald, S. L. J. Am. Chem. Soc. 2005, 127, 4685-4696.
27. (g) Pastine, S. J.; Gribkov, D. V.; Sames, D. J. Am. Chem. Soc. 2006, 128, 14220-14221.
28. (h) Lafrance, M.; Gorelsky, S. I.; Fagnou, K. J. Am. Chem. Soc. 2007, 129, 14570-14571.
29. (i) Watanabe, T.; Oishi, S.; Fujii, N.; Ohno, H. Org. Lett. 2008, 10, 1759-1762.
30. 2Ph was reported to be 24.3 in dimethyl sulfoxide at 25 °C. See: Bordwell, F. G. Acc. Chem. Res. 1988, 27, 456-463.
31. Xanthene (6) was formed through the reduction of xanthenyl cation with the remaining sodium cyanoborohydride in the same pot. No xanthenyl alcohol, which could be generated by the nucleophilic attack of hydroxide to the cation, was observed.
32. Heitz, W.; Brugging, W.; Freund, L.; Gailberger, M.; Greiner, A.; Jung, H.; Kampschulte, U.; Niessner, N.; Osan, F.; Schmidt, H. W.; Wicker, M. Makromol. Chem. 1988, 189, 119-127.