New 2-(2-pyridyl)piperidines: synthesis, complexation of palladium and catalytic activity in Suzuki reaction

Tetrahedron Letters

Volumn 49, Issue 10, 2008, Pages 1706-1709

  Puget, Bertrand ^a   Roblin, Jean Philippe ^a   Prim, Damien ^b   Troin, Yves ^a  

^a Ecole Nationale Superieure de Chimie de Clermont Ferrand   (France)

^b UNIVERSITÉ DE VERSAILLES SAINT QUENTIN EN YVELINES   (France)

Author keywords

[No Author keywords available]

Indexed keywords

2 (2 PYRIDYL)PIPERIDINE DERIVATIVE; DIAMINE; PALLADIUM; PIPERIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; COMPLEX FORMATION; MANNICH REACTION; QUANTITATIVE ANALYSIS; SUZUKI REACTION; SYNTHESIS;

EID: 38949171295     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.12.125     Document Type: Article

References (31)

1. Lucet D., Gall T.L., and Mioskowski C. Angew. Chem., Int. Ed. 37 (1998) 2580
2. Kubota H., Kakefuda A., Watanabe T., Ishii N., Wada K., Masuda N., Sakamoto S., and Tsukamoto S.-I. J. Med. Chem. 46 (2003) 4728
3. For selected examples see:. Kim H., Yen C., Preston P., and Chin J. Org. Lett. 8 (2006) 5239
4. Alexakis A., and Andrey O. Org. Lett. 4 (2002) 3611
5. Betancort J.M., and Barbas III C.F. Org. Lett. 3 (2001) 3737
6. Alexakis A., Tomassini A., Chouillet C., Roland S., Mangeney P., and Bernardelli G. Angew. Chem., Int. Ed. 39 (2000) 4093
7. For selected examples see:. Li X., Hewgley J.B., Mulrooney C.A., Yang J., and Kozlowski M.C. J. Org. Chem. 68 (2003) 5500
8. Ohkuma T., koizumi M., Muniz K., Hilt G., Kabuto C., and Noyori R. J. Am. Chem. Soc. 124 (2002) 6508
9. Keller L., Vargas Sanchez M., Prim D., Couty F., Evano G., and Marrot J. J. Organomet. Chem. 690 (2005) 2306
10. Ciblat S., Besse P., Canet J.-L., Veschambre H., Troin Y., and Gelas J. Tetrahedron: Asymmetry 10 (1999) 2225-2235
11. Ciblat S., Besse P., Papastergiou V., Veschambre H., Canet J.-L., and Troin Y. Tetrahedron: Asymmetry 11 (2000) 2221-2229
12. Ciblat S., Calinaud P., Canet J.-L., and Troin Y. J. Chem. Soc., Perkin Trans. 1 (2000) 353-357
13. Carbonnel S., and Troin Y. Heterocycles 57 (2002) 1807-1830
14. Rougnon-Glasson S., Tratrat C., Chalard P., Canet J.-L., and Troin Y. Tetrahedron: Asymmetry 15 (2004) 1561-1567
15. For successful application of our methodology in enantioselective synthesis of (-)-indolizidine 209B, see:. Davis F.A., and Yang B. Org. Lett. 5 (2003) 5011-5014
16. Miyaura N., and Suzuki A. Chem. Rev. 95 (1995) 2457-2483
17. Stanforth S.P. Tetrahedron 54 (1998) 263-303
18. Suzuki A. Metal-catalysed Cross-coupling Reactions. In: Diederich F., and Stang P.J. (Eds) (1998), Wiley-VCH, Weinheim, Germany 49-97
19. Suzuki A. J. Organomet. Chem. 576 (1999) 147
20. Hassan J., Sévignon M., Schulz M., and Lemaire M. Chem. Rev. 102 (2002) 1359-1469
21. Alonso D.A., Najera C., and Pecheco M.C. J. Org. Chem. 67 (2002) 5588-5594
22. Najera C., Gil-Molto J., and Karlstrom S. Adv. Synth. Catal. 346 (2004) 1798-1811
23. Mino T., Shirae Y., Sakamoto M., and Fujita T. J. Org. Chem. 70 (2005) 2191-2194
24. Cui X., Zhou Y., Wang N., Liu L., and Guo Q.-X. Tetrahedron Lett. 48 (2007) 163-167
25. Takemoto T., Iwasa S., Hamada H., Shibatomi K., Kameyama M., Motoyama Y., and Nishiyama H. Tetrahedron Lett. 48 (2007) 3397-3401
26. Li S., Lin Y., Cao J., and Zhang S. J. Org. Chem. 72 (2007) 4067-4072
27. Munchof M.J., and Meyers A.I. J. Am. Chem. Soc. 117 (1995) 5399-5400
28. 3) 155.6, 149.2, 137.9, 124 122.6, 62.2, 60.3, 30.3, 30.1, 23.3, 22.5, 19.4, 16.7.
29. Dunina V.V., Kuz'mina L.G., Kazakova M.Y., Gorunova O.N., Grishin Y.K., and Kazakova E.I. Eur. J. Inorg. Chem. (1999) 1029
30. 6) 149.9, 139.4, 123.5, 120.4, 71.1, 70.6, 34.8, 28.8, 26.0, 24.5, 20.4, 19.7.
31. 2O (95:5) freshly prepared with degassed and distilled solvents was stirred at 110 °C for 30 min. After the mixture was washed with water, extracted with ether, dried over magnesium sulfate and concentrated under vacuum, the residue was purified by flash column chromatography (petroleum ether) to afford biphenyl-4-carbaldehyde 11 (82 mg, 90%).