Testing phosphanes in the palladium-catalysed allylation of secondary and primary amines

European Journal of Inorganic Chemistry

Volumn , Issue 19, 2006, Pages 3911-3922

  Thoumazet, Claire ^a   Grützmacher, Hansjörg ^b   Deschamps, Bernard ^a   Ricard, Louis ^a   Le Floch, Pascal ^a  

^a LABORATOIRE HÉTÉROÉLÉMENTS ET COORDINATION   (France)

^b ETH ZURICH   (Switzerland)

Author keywords

Allylation; Amines; Catalysis; Palladium; Phosphorus

Indexed keywords

ALLYLATION; AMINES; CATALYSIS; CATALYSTS; LIGANDS; PHOSPHORUS;

ALLYLIC ALCOHOL; BIDENTATE LIGANDS; ELECTRONIC NATURES; MONODENTATE LIGANDS; PALLADIUM-CATALYZED; PHOSPHANES; PHOSPHOLES; SECONDARY AND PRIMARY AMINES; ]+ CATALYST; Π-ACCEPTORS;

PALLADIUM;

EID: 33749859607     PISSN: 14341948     EISSN: 10990682     Source Type: Journal    
DOI: 10.1002/ejic.200600592     Document Type: Article

References (59)

1. a) B. M. Trost, Chem. Pharm. Bull. 2002, 50, 1-14;
2. b) M. Johannsen, K. A. Jorgensen, Chem. Rev. 1998, 98, 1689-1708;
3. c) B. M. Trost, D. L. Van Vranken, C. Bingel, J. Am. Chem. Soc. 1992, 114, 9327-9343;
4. d) B. M. Trost, in: Advances in Natural Product Chemistry (Ed.: Atta-Ur-Rahman), Harwood Academic Publishers, Harwood, 1992, pp. 19-34;
5. e) S. A. Godleski, in: Comprehensive Organic Synthesis, vol. 4 (Eds.: B. M. Trost, I. Fleming), Pergamon Press, New York, 1991, pp. 585-661.
6. a) B. M. Trost, D. L. Van Vranken, Chem. Rev. 1996, 96, 395-422;
7. b) B. M. Trost, F. D. Toste, A. B. Pinkerton, Chem. Rev. 2001, 101, 2067-2096;
8. c) S. A. Godleski, in: Comprehensive Organic Synthesis, vol. 4, chapter 3.3 (Eds.: B. M. Trost, I. Fleming, M. F. Semmelhack), Pergamon Press, Oxford, 1990;
9. d) J. A. Davis, in: Comprehensive Organometallic Chemistry II, vol. 9 (Eds.: E. W. Abel, F. G. A. Stone, G. Wilkinson), Pergamon, Oxford, 1995, p. 291;
10. e) J. Tsuji, Transition Metal Reagents and Catalysts, Wiley, New York, 2000;
11. f) B. M. Trost, Science 1991, 254, 1471;
12. g) B. M. Trost, Angew. Chem. Int. Ed. Engl. 1995, 34, 259-281.
13. a) J. C. Hierso, A. Fihri, R. Amardeil, P. Meunier, H. Doucet, M. Santelli, Tetrahedron 2005, 61, 9759-9766;
14. b) M. Feuerstein, D. Laurenti, H. Doucet, M. Santelli, Tetrahedron Lett. 2001, 42, 2313-2315;
15. c) J. Tsuji, Palladium Reagents and Catalysis: Innovations in Organic Synthesis Wiley, Chichester, 1995, p. 292;
16. d) T. Ohmura, J. F. Hartwig, J. Am. Chem. Soc. 2002, 124, 15164-15165;
17. e) T. Ohmura, J. F. Hartwig, J. Am. Chem. Soc. 2003, 125, 3426-3427;
18. f) R. Kuwano, K. I. Uchida, Y. Ito, Org. Lett. 2003, 5, 2177-2179.
19. a) F. Ozawa, H. Okamoto, S. Kawagishi, S. Yamamoto, T. Minami, M. Yoshifuji, J. Am. Chem. Soc. 2002, 124, 10968-10969;
20. b) F. Ozawa, T. Ishiyama, S. Yamamoto, S. Kawagishi, H. Murakami, M. Yoshifuji, Organometallics 2004, 23, 1698-1707;
21. c) H. Bricout, J.-F. Carpentier, A. Mortreux, J. Mol. Catal. A 1998, 136, 243-251;
22. d) M. Kimura, M. Futamata, K. Shibata, Y. Tamaru, Chem. Commun. 2003, 234-235;
23. e) M. Sakaibara, A. Ogawa, Tetrahedron Lett. 1994, 35, 8013-8014;
24. f) S. C. Yang, Y. C. Tsai, Organometallics 2001, 20, 763-770;
25. g) Y. Tamaru, J. Organomet. Chem. 1999, 576, 215-231.
26. O. Piechaczyk, M. Doux, L. Ricard, P. Le Floch, Organometallics 2005, 24, 1204-1213.
27. For the synthesis see B. Lukas, R. M. G. Roberts, J. Silver, A. S. Wells, J. Organomet. Chem. 1983, 256, 103-110.
28. For applications in catalysis see: a) C. Bergounhou, D. Neibecker, R. Réau, J. Chem. Soc., Chem. Commun. 1988, 1370-1372;
29. b) D. Neibecker, R. Réau, S. Lecolier, J. Org. Chem. 1989, 54, 5208-5210;
30. c) D. Neibecker, R. Réau, J. Mol. Catal. 1989, 50, 153-163;
31. d) D. Neibecker, R. Réau, New J. Chem. 1991, 15, 279-281;
32. e) A. Polo, C. Claver, S. Castillon, A. Ruiz, J. C. Bayon, J. Real, C. Mealli, D. Masi, Organometallics 1992, 11, 3525-3533;
33. f) L. M. Wilkes, J. H. Nelson, L. B. McCusker, K. Seff, F. Mathey, Inorg. Chem. 1983, 22, 2476-2485.
34. S. Affandi, R. L. Green, B. T. Hsieh, M. S. Holt, J. H. Nelson, Synth. React. Inorg. Met. Org. Chem. 1987, 17, 307-318.
35. S. Bousquet, J. J. Brunet, T. Courcet, D. Neibecker, Phosphorus Sulfur Silicon Relat. Elem. 1998, 142, 117-124.
36. C. Thoumazet, L. Ricard, H. Grutzmacher, P. Le Floch, Chem. Commun. 2005, 1592-1594.
37. a) S. Ogoshi, M. Morita, H. Kurosawa, J. Am. Chem. Soc. 2003, 125, 9020-9021;
38. b) S. Ogoshi, K. Tsutsumi, H. Kurosawa, J. Organomet. Chem. 1995, 493, C19-C21;
39. c) M. W. Baize, P. W. Blosser, V. Plantevin, D. G. Schimpff, J. C. Gallucci, A. Wojcicki, Organometallics 1996, 15, 164-173.
40. a) W. P. Ozbirn, R. A. Jacobson, J. C. Clardy, J. Chem. Soc., Chem. Commun. 1971, 1062;
41. b) E. C. Alyea, G. Ferguson, J. F. Gallagher, Acta Crystallogr., Sect. C 1992, 48, 959-961.
42. F. Mathey, Phosphorus-Carbon Heterocyclic Chemistry: The Rise of a New Domain, chapter 4, Pergamon Press, Amsterdam, 2001, p. 219.
43. E. Mattmann, F. Mathey, A. Sevin, G. Frison, J. Org. Chem. 2002, 67, 1208-1213.
44. W. Egan, R. Tang, G. Zon, K. Mislow, J. Am. Chem. Soc. 1971, 93, 6205-6216.
45. a) A. Dransfeld, L. Nyulaszi, P. v. R. Schleyer, Inorg. Chem. 1998, 37, 4413-4420;
46. b) P. v. R. Schleyer, C. Maerker, A. Dransfeld, H. J. Jiao, N. Hommes, J. Am. Chem. Soc. 1996, 118, 6317-6318;
47. c) L. Nyulaszi, Chem. Rev. 2001, 101, 1229-1246;
48. d) M. K. Cyranski, T. M. Krygowski, A. R. Katritzky, P. v. R. Schleyer, J. Org. Chem. 2002, 67, 1333-1338;
49. e) P. Schleyer, Chem. Rev. 2001, 101, 1115-1117.
50. G. Frenking, N. Frölich, Chem. Rev. 2000, 100, 717-774.
51. D. Drew, J. R. Doyle, in: Inorganic Syntheses, vol. 28 (Ed.: R. J. Angelici), 1990, pp. 348-349.
52. M. Zettlitzer, H. tom Dieck, E. T. K. Haupt, L. Stamp, Chem. Ber. 1986, 119, 1868-1875.
53. Gaussian 03 Revision C.02, M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, J. A. Montgomery Jr, T. Vreven, K. N. Kudin, J. C. Burant, J. M. Millam, S. S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G. A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J. E. Knox, H. P. Hratchian, J. B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, P. Y. Ayala, K. Morokuma, G. A. Voth, P. Salvador, J. J. Dannenberg, V. G. Zakrzewski, S. Dapprich, A. D. Daniels, M. C. Strain, O. Farkas, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. V. Ortiz, Q. Cui, A. G. Baboul, S. Clifford, J. Cioslowski, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, M. Challacombe, P. M. W. Gill, B. Johnson, W. Chen, M. W. Wong, C. Gonzalez, and J. A. Pople, Gaussian, Inc., Wallingford CT, 2004.
54. a) A. D. J. Becke, J. Phys. Chem. 1993, 98, 5648-5662;
55. b) J. P. Perdew, Y. Wang, Phys. Rev. B 1992, 45, 13244-13249.
56. [21]a) S. I. Gorelsky, AOMIX: Program for Molecular Orbital Analysis, http://www.sg-chem.net/, York University: Toronto, Canada, 1997;
57. b) S. I. Gorelsky, J. Organomet. Chem. 2001, 635, 187-196.
58. A. Altomare, M. C. Burla, M. Camalli, G. Cascarano, C. Giacovazzo, A. Guagliardi, A. G. G. Moliterni, G. Polidori, R. Spagna, SIR97, An Integrated Package of Computer Programs for the Solution and Refinement of Crystal Structures using Single Crystal Data.
59. G. M. Sheldrick, SHELXL-97, University of Göttingen, Göttingen, Germany, 1997.