N-heterocyclic carbene-palladium catalysts for the bisdiene cyclization-trapping reaction with sulfonamides under thermal and microwave conditions

Journal of Organometallic Chemistry

Volumn 690, Issue 24-25, 2005, Pages 6205-6209

  Takacs, James M ^a   Venkataraman, Somasundaram ^a   Andrews, Ross N ^a   Pelter, Libbie S W ^b  

^a UNIVERSITY OF NEBRASKA LINCOLN   (United States)

^b PURDUE UNIVERSITY CALUMET   (United States)

Author keywords

Catalysis; Microwave irradiation; N heterocyclic carbene ligands; Palladium

Indexed keywords

CATALYSTS; IRRADIATION; MICROWAVES; REACTION KINETICS; THERMOANALYSIS;

MICROWAVE IRRADIATION; N-HETEROCYCLIC CARBENE LIGANDS; THERMAL CONDITIONS;

PALLADIUM;

EID: 27744509824     PISSN: 0022328X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jorganchem.2005.08.048     Document Type: Article

References (40)

1. J.M. Takacs E.-i. Negishi Handbook of Organopalladium Chemistry for Organic Synthesis vol. 1 2002 Wiley New York 1579
2. A. Behr Aspects Homogeneous Catal. 5 1984 3
3. G.P. Chiusoli, M. Costa, L. Pallini, and G. Terenghi Transit. Met. Chem. (Weinheim, Ger.) 7 1982 304
4. R.N. Fakhretdinov, R.N. Khusnitdinov, I.B. Abdrakhmanov, and U.M. Dzhemilev Zh. Org. Khim. 20 1984 1101
5. U.M. Dzhemilev, R.I. Khusnutdinov, Z.S. Muslimov, G.A. Tolstikov, and O.M. Nefedov Izv. Akad. Nauk SSSR, Ser. Khim 1980 220
6. J. Tsuji, and M. Takahashi J. Mol. Catal. 10 1980 107
7. J. Beger, and F. Meier J. Prakt. Chem. 322 1980 69
8. U.M. Dzhemilev, G.A. Tolstikov, A.G. Telin, M.Y. Dolomatov, E.G. Galkin, and G.A. Tolstikov Izv. Akad. Nauk SSSR, Ser. Khim 1980 163
9. R.M. Safuanova, R.N. Fakhretdinov, and U.M. Dzhemilev Izv. Akad. Nauk SSSR, Ser. Khim 4 1988 821
10. R.M. Safuanova, R.N. Fakhretdinov, and U.M. Dzhemilev Izv. Akad. Nauk SSSR, Ser. Khim 3 1984 703
11. Y. Inoue, M. Taguchi, M. Toyofuku, and H. Hashimoto Bull. Chem. Soc. Jpn. 57 1984 3021
12. U.M. Dzhemilev, R.N. Fakhretdinov, and R.M. Safuanova Izv. Akad. Nauk SSSR, Ser. Khim 9 1985 2098
13. M.I. Zakharkin, V.V. Guseva, D.D. Sulaimankulova, and E.A. Petrushkina Zh. Org. Khim. 23 1987 1654
14. E.A. Petrushkina, V.I. Bregadze, Y.F. Oprunenko, T.M. Shcherbina, and A.P. Laretina Metalloorg. Khim. 4 1991 1336
15. U.M. Dzhemilev, M.M. Sirazova, R.V. Kunakova, A.A. Panasenko, and L.M. Khalilov Izv. Akad. Nauk SSSR, Ser. Khim 2 1985 372
16. U.M. Dzhemilev, R.V. Kunakova, and M.M. Sirazova Izv. Akad. Nauk SSSR, Ser. Khim 12 1985 2766
17. J.M. Takacs, and J. Han Org. Lett. 6 2004 3099
18. J.M. Takacs, and J. Zhu J. Org. Chem. 54 1989 5193
19. Thus far, these latter reactions have only been carried out at a catalyst loading of 2% palladium.
20. F.K. Zinn, M.S. Viciu, and S.P. Nolan Annu. Rep. Prog. Chem., Sect. B, Org. Chem. 100 2004 231
21. W.A. Herrmann Angew. Chem., Int. Ed. 41 2002 1290
22. A.C. Hillier, and S.P. Nolan Plat. Met. Rev. 46 2002 50
23. H.A. Duong, M.J. Cross, and J. Louie J. Am. Chem. Soc. 126 2004 11438
24. G.M. Mahandru, G. Liu, and J. Montgomery J. Am. Chem. Soc. 126 2004 3698
25. Y. Sato, N. Imakuni, and M. Mori Adv. Synth. Catal. 345 2003 488
26. M. Lautens, and J. Mancuso Synlett 2002 394
27. Y. Sato, R. Sawaki, and M. Mori Organometallics 20 2001 5510
28. R. Jackstell, G.A. Andreu, A. Frisch, K. Selvakumar, A. Zapf, H. Klein, A. Spannenberg, D. Rottger, O. Briel, R. Karch, and M. Beller Angew. Chem., Int. Ed. 41 2002 986
29. R. Jackstell, A. Frisch, M. Beller, D. Rottger, M. Malaun, and B. Bildstein J. Mol. Catal. A: Chem. 185 2002 105
30. M.S. Viciu, F.K. Zinn, E.D. Stevens, and S.P. Nolan Organometallics 22 2003 3175
31. R. Jackstell, S. Harkal, H. Jiao, A. Spannenberg, C. Borgmann, D. Roettger, F. Nierlich, M. Elliot, S. Niven, K. Cavell, O. Navarro, M.S. Viciu, S.P. Nolan, and M. Beller Chem. Eur. J. 10 2004 3891
32. J.M. Takacs, S. Layek, H. Palencia, R.N. Andrews, Adv. Synth. Catal. 347 (2005) in press.
33. M.S. Viciu, O. Navarro, R.F. Germaneau, R.A. Kelly III, W. Sommer, N. Marion, E.D. Stevens, L. Cavallo, and S.P. Nolan Organometallics 23 2004 1629
34. A. de la Hoz, A. Diaz-Ortiz, and A. Moreno Chem. Soc. Rev. 34 2005 164
35. C.O. Kappe Angew. Chem., Int. Ed. 43 2004 6250
36. B.L. Hayes Aldrichim. Acta 37 2004 66
37. See, for example: O. Navarro, H. Kaur, P. Mahjoor, and S.P. Nolan J. Org. Chem. 69 2004 3173
38. A.J. McCarroll, D.A. Sandham, L.R. Titcomb, A.K.d.K. Lewis, F.G.N. Cloke, B.P. Davies, A. Perez de Santana, W. Hiller, and S. Caddick Mol. Divers. 7 2003 115
39. A. Furstner, F. Stelzer, A. Rumbo, and H. Krause Chem. Eur. J. 8 2002 1856
40. + 565.2195, found 565.2186.