Carbon-carbon bond formations at the benzylic positions of N-benzylxanthone imines and N-benzyldi-1-naphthyl ketone imine

Tetrahedron

Volumn 65, Issue 26, 2009, Pages 5125-5131

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

^a KYOTO UNIVERSITY   (Japan)

Author keywords

Benzylic alkylation; Benzylic arylation; Deprotonation; N Benzyl imines; Palladium

Indexed keywords

4 BENZOYLAMINO N,N DIETHYL 4 PHENYLBUTANAMIDE; BENZYLAMINE DERIVATIVE; CARBON; IMINE; N (1 PHENYLPENTYL)BENZAMIDE; N (1,2 DIPHENYLETHYL)BENZAMIDE; N (2 CYCLOPROPYL 1 PHENYLETHYL)BENZAMIDE; N (2 METHYL 1 PHENYLBUTYL)BENZAMIDE; N (3 METHYL 1 PHENYL 3 BUTENYL)BENZAMIDE; N (4 METHYL 1 PHENYL 3 PENTENYL)BENZAMIDE; N (DI 1 NAPHTHYLMETHYLIDENE)BENZYLAMINE; N [(E) 1 PHENYL 3 PENTENYL]BENZAMIDE; N [(E) 1,4 DIPHENYL 3 BUTENYL]BENZAMIDE; PALLADIUM; UNCLASSIFIED DRUG;

ARTICLE; ARYLATION; CATALYSIS; CHEMICAL BOND; CHEMICAL REACTION; CHEMICAL STRUCTURE; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; SUZUKI REACTION; SYNTHESIS;

EID: 65749120740     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2009.02.034     Document Type: Article

References (41)

1. Reviews:
2. Beak P., Zajdel W.J., and Reitz D.B. Chem. Rev. 84 (1984) 471-523
3. Gawley R.E. Curr. Org. Chem. 1 (1997) 71-94
4. O'Donnell M.J. Acc. Chem. Res. 37 (2004) 506-517
5. A part of this work was communicated:. Niwa T., Yorimitsu H., and Oshima K. Org. Lett. 10 (2008) 4689-4691
6. α-Arylation of carbonyls:
7. Culkin D.A., and Hartwig J.F. Acc. Chem. Res. 36 (2003) 234-245
8. Hamann B.C., and Hartwig J.F. J. Am. Chem. Soc. 119 (1997) 12382-12383
9. Palucki M., and Buchwald S.L. J. Am. Chem. Soc. 119 (1997) 11108-11109
10. Satoh T., Inoh J., Kawamura Y., Kawamura Y., Miura M., and Nomura M. Bull. Chem. Soc. Jpn. 71 (1998) 2239-2246
11. Muratake H., and Natsume M. Tetrahedron Lett. 38 (1997) 7581-7582
12. Intermolecular arylation at the activated benzylic or allylic positions:
13. Inoh J., Satoh T., Pivsa-Art S., Miura M., and Nomura M. Tetrahedron Lett. 39 (1998) 4673-4676
14. Dyker G., Heiermann J., Miura M., Inoh J., Pivsa-Art S., Satoh T., and Nomura M. Chem.-Eur. J. 6 (2000) 3426-3433
15. Dyker G., Heiermann J., and Miura M. Adv. Synth. Catal. 345 (2003) 1127-1132
16. Niwa T., Yorimitsu H., and Oshima K. Org. Lett. 9 (2007) 2373-2375
17. Mousseau J.J., Larivée A., and Charette A.B. Org. Lett. 10 (2008) 1641-1643
18. Campeau L.-C., Schipper D.J., and Fagnou K. J. Am. Chem. Soc. 130 (2008) 3266-3267
19. Intramolecular arylative cyclization at the benzylic positions:
20. Ren H., and Knochel P. Angew. Chem., Int. Ed. 45 (2006) 3462-3465
21. Ren H., Li Z., and Knochel P. Chem. Asian J. 2 (2007) 416-433
22. Dong C.-G., and Hu Q.-S. Angew. Chem., Int. Ed. 45 (2006) 2289-2292
23. Hu Q.-S. Synlett (2007) 1331-1345
24. Catellani M., Motti E., and Ghelli S. Chem. Commun. (2000) 2003-2004
25. Salcedo A., Neuville L., and Zhu J. J. Org. Chem. 73 (2008) 3600-3603
26. Arylation of N-tert-butylhydrazones as an acyl anion equivalent:. Takemiya A., and Hartwig J.F. J. Am. Chem. Soc. 128 (2006) 14800-14801
27. 3)-H arylation involving cleavage of less acidic hydrogens:
28. Zaitsev V.G., Shabashov D., and Daugulis O. J. Am. Chem. Soc. 127 (2005) 13154-13155
29. Shabashov D., and Daugulis O. Org. Lett. 7 (2005) 3657-3659
30. Reddy B.V.S., Reddy L.R., and Corey E.J. Org. Lett. 8 (2006) 3391-3394
31. Kalyani D., Deprez N.R., Desai L.V., and Sanford M.S. J. Am. Chem. Soc. 127 (2005) 7330-7331
32. Giri R., Maugel N., Li J.-J., Wang D.-H., Breazzano S.P., Saunders L.B., and Yu J.-Q. J. Am. Chem. Soc. 129 (2007) 3510-3511
33. Barder T.E., Walker S.D., Martinelli J.R., and Buchwald S.L. J. Am. Chem. Soc. 127 (2005) 4685-4696
34. Pastine S.J., Gribkov D.V., and Sames D. J. Am. Chem. Soc. 128 (2006) 14220-14221
35. Lafrance M., Gorelsky S.I., and Fagnou K. J. Am. Chem. Soc. 129 (2007) 14570-14571
36. Watanabe T., Oishi S., Fujii N., and Ohno H. Org. Lett. 10 (2008) 1759-1762
37. 2Ph was reported to be 24.3 in dimethyl sulfoxide at 25 °C. See:. Bordwell F.G. Acc. Chem. Res. 21 (1988) 456-463
38. Heitz W., Brugging W., Freund L., Gailberger M., Greiner A., Jung H., Kampschulte U., Niessner N., Osan F., Schmidt H.W., and Wicker M. Makromol. Chem. 189 (1988) 119-127
39. Gainelli G., Giacomini D., Treré A., and Boyl P.P. J. Org. Chem. 61 (1996) 5134-5139
40. Roy U.K., and Roy S. Tetrahedron Lett. 48 (2007) 7177-7180
41. Miller R.D., and Goelitz P. J. Org. Chem. 46 (1981) 1616-1618