Cationic (η1-allyl)-palladium complexes as feasible intermediates in catalyzed reactions

Organometallics

Volumn 25, Issue 15, 2006, Pages 3611-3618

  García Iglesias, Miguel ^a   Buñuel, Elena ^a   Cárdenas, Diego J ^a  

^a UNIVERSIDAD AUTÓNOMA DE MADRID   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDES; CATALYSIS; CATIONIC POLYMERIZATION; COMPLEXATION; OLEFINS; ORGANOMETALLICS; POSITIVE IONS; REACTION KINETICS;

CATALYZED REACTIONS; CYCLOMETALATING LIGANDS; FEASIBLE INTERMEDIATES; NEUTRAL COMPLEXES;

PALLADIUM COMPOUNDS;

EID: 33746347045     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om060199+     Document Type: Article

References (93)

1. (a) Metal-catalyzed Cross-coupling Reactions; Diederich, F., Stang, P. J., Eds.; Wiley-VCH: Weinheim, 1998.
2. (b) Metal-catalyzed Crosscoupling Reactions; de Meijere, A., Diederich, F., Eds.; Wiley-VCH; Weinheim, 2004.
3. Palladium Reagents and Catalysts Innovations in Organic Synthesis; Tsuji, J., Ed.; Wiley: Chichester, 1997.
4. Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E., Ed.; Wiley: New York, 2002.
5. Cárdenas, D. J.; Echavarren, A. New J. Chem. 2004, 28, 338-347.
6. Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E., Ed.; Wiley: New York, 2002; Vol. 2, Chapter V.2.1, pp 1669-1844.
7. Asymmetric allylation of nucleophiles: Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E., Ed.; Wiley: New York, 2002; Vol. 2, Chapter V.2.4, pp 1945-1980.
8. (a) Vasse, J. L.; Stranne, R.; Zalubovskis, R.; Gayet, C.; Moberg, C. J. Org. Chem. 2003, 68, 3258-3270.
9. (b) García-Mancheño, O.; Priego, J.; Cabrera, S.; Gómez-Arrayás, R.; Llamas, T.; Carretero, J. C. J. Org. Chem. 2003, 68, 3679-3686.
10. (c) Trost, B. M.; Lee, C. B. J. Am. Chem. Soc. 2001, 123, 3671.
11. Asymmetric allylation of nucleophiles: Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E., Ed.; Wiley: New York, 2002; Vol. 2. Chapter V.2.4, pp 1945-1980.
12. (a) Hegedus, L. S.; Darlington, W. H.; Russell, C. E. J. Org. Chem. 1980, 45, 5193-5196.
13. (b) Hoffmann, H. M. R.; Otte, A. R.; Wilde, A.; Menzer, S.; Williams, D. J. Angew. Chem., Int. Ed. Engl. 1995, 34, 100-102.
14. (c) Wilde, A.; Otte, A. R.; Hoffmann, H. M. R. J. Chem. Soc., Chem. Commun. 1993, 615-616.
15. (d) Hoffmann, H. M. R.; Otte, A. R.; Wilde, A. Angew. Chem., Int. Ed. Engl. 1992, 31, 234-236.
16. (e) Carfagna, C.; Mariani, L.; Museo, A.; Sallese, G.; Santi, R. J. Org. Chem. 1991, 56, 3924-3927.
17. (f) Carfagna, C.; Galarini, R.; Musco, A. J. Mol. Catal. 1992, 72, 19-27.
18. (a) Aranyos, A.; Szabó, K. J.; Castaño, A. M.; Bäckvall, J.-E. Organometallics 1997, 16, 1058-1064.
19. (b) Castaño, A. M.; Aranyos, A.; Szabó, K. J.; Bäckvall, J.-E. Angew. Chem., Int. Ed. Engl. 1995, 34, 2551-2553.
20. (c) Szabó, K. J. Organometallics 1996, 15, 1128-1133.
21. (a) Szabó, K. J. Chem. Soc. Rev. 2001, 30, 136-143.
22. (b) Delbecq, F.; Lapouge, C. Organometallics 2000, 19, 2716-2723.
23. (c) V. Branchadell, V.; Moreno-Mañas, M.; Pleixats, R. Organometallics 2002, 21, 2407-2412.
24. (d) Branchadell, V.; Moreno-Mañas, M.; Pajuelo, F.; Pleixats, R. Organometallics 1999, 18, 4934-4941.
25. (e) Hagelin, H.; Åkermark, B.; Norrby, P.-O. Chem. Eur. J. 1999, 5, 902-909.
26. (f) Szabó, K. Organometallics 1996, 15, 1128-1133.
27. (g) Ward, T. R. Organometallics 1996, 15, 2836-2838.
28. (h) Bloechl, P. E.; Togni, A. Organometallics 1996, 75, 4125-4132.
29. (i) Senn, H. M.; Bloechl, P. E.; Togni, A. J. Am. Chem. Soc. 2000, 122, 4098-4107.
30. (a) Hagelin, H.; Åkermark, B.; Norrby, P.-O. Organometallics 1999, 18, 2884-2895.
31. (b) M. Kollmar, M.; Steinhagen, H.; Janssen, J. P.; Goldfuss, B.; Malinovskaya, S. A.; Vázquez, J.; Rominger, F.; Heimchen, G. Chem. Eur. J. 2002, 8, 3103-3114.
32. (c) Kollmar, M.; Goldfuss, B.; Reggelin, M.; Rominger, F.; Helmehen, G. Chem. Eur. J. 2001, 7, 4913-4927.
33. (d) Widhalm, M.; Nettekoven, U.; Kalchhauser, H.; Mereiter, K. L.; Calhorda, M.; Félix, J. V. Organometallics 2002, 21, 315-325.
34. Reviews: (a) Oppolzer, W.; Flachsmann, F. Helv. Chim. Acta 2001, 84, 416-430.
35. (b) Reference 3, Vol. 1, Chapter IV.4, pp 1845-1886.
36. (c) Oppolzer, W. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford: 1991; Vol. 5, Chapter 1.2.
37. (d) Oppolzer, W. In Comprehensive Organometallic Chemistry II; Abel, E. W. F., Stone, G. A., Wilkinson, G., Eds.; Pergamon: Oxford: 1995; Vol. 12, Chapter 8.3.
38. Oppolzer, W. Pure Appl. Chem. 1988, 60, 39.
39. (e) A. Heumann, A.; Réglier, M. Tetrahedron 1995, 57, 975-1015.
40. Tamara, Y. J. Organomet. Chem. 1999, 576, 215-231.
41. (a) Trost, B. M.; Keinan, E. Tetrahedron Lett. 1980, 21, 2595-2598.
42. (b) Keinan, E.; Peretz, M. J. Org. Chem. 1983, 48, 5302-5309.
43. (c) Coupling of stannanes with allyl phosphates: Kosugi, M.; Ohashi, K.; Akuzawa, K.; Kawazoe, T.; Sano, T.; Migita, T. Chem. Lett. 1987, 1237-1238.
44. (d) Godschalx, J.; Stille, J. K. Tetrahedron Lett. 1980, 21, 2599-2602.
45. (e) Frans, R. J.; Nicholas, K. M. Organometallics 2000, 19, 1458-1460.
46. Terakado, M.; Miyazawa, M.; Yamamoto, K. Synlett 1994, 134-136.
47. Méndez, M.; Cuerva, J. M.; Gómez-Bengoa, E.; Cárdenas, D. J.; Echavarren, A. M. Chem. Eur. J. 2002, 8, 3620-3628.
48. (a) Krause, J.; Goddard, R.; Mynott, R.; Pörschke, K.-R. Organometallics 2001, 20, 1992-1999.
49. (b) Krause, J.; Bonrath, W.; Pörschke, K.-R. Organometallics 1992, 11, 1158-1167.
50. (a) Nakamura, H.; Iwama, H.; Yamamoto, Y. J. Am. Chem. Soc. 1996, 118, 6641-6647.
51. (b) Nakamura, H.; Shim, J.-G.; Yamamoto, Y. J. Am. Chem. Soc. 1997, 119, 8113-8114.
52. (c) Nakamura, H.; Bao, M.; Yamamoto, Y. Angew. Chem., Int. Ed. 2001, 40, 3208-320.
53. (a) Solin, N.; Narayan, S.; Szabó, K. J. Org. Lett. 2001, 3, 909-912.
54. (b) Solin, N.; Narayan, S.; Szabó, K. J. J. Org. Chem. 2001, 66, 1686-1693.
55. (a) Wallner, O. A.; Szabó, K. J. Chem. Eur. J. 2003, 9, 4025-4030.
56. (b) Wallner, O. A.; Szabó, K. J. J. Org. Chem. 2003, 68, 2934-2943.
57. (c) Wallner, O. A.; Szabó, K. J. Org. Lett. 2002, 4, 1653-1566.
58. (d) Szabó, K. J. Chem. Eur. J. 2000, 6, 4413-4421.
59. (a) Kuhn, O.; Mayr, H. Angew. Chem., Int Ed. 1999, 38, 343-346.
60. (b) Benn, R.; Jolly, P. W.; Mynott, R.; Raspel, B.; Schenker, O.; Schick, K. P.; Schroth, G. Organometallics 1985, 4, 1945-1953.
61. (a) Solin, N.; Wallner, O. A.; Szabó, K. J. Org. Lett. 2005, 7, 689-691.
62. (b) Sebelius, S.; Wallner, O. A.; Szabó, K. J. Org. Lett. 2003, 5, 3065-3068.
63. Wallner, O. A.; Szabó, K. J. Org. Lett. 2004, 6, 1829-1831.
64. Solin, N.; Kjellgren, J.; Szabó, K. J. J. Am. Chem. Soc. 2004, 126, 7026-7033.
65. (a) Solin, N.; Szabó, K. J. Organometallics 2001, 20, 5464-5471.
66. (b) Rülke, R. E.; Kaasjager, V. E.; Wehman, P.; Elsevier: C. J.; van Leeuwen, P. W. N. M.; Vrieze, K.; Fraanje, J.; Goubitz, K.; Spek, A. L. Organometallics 1996, 15, 3022-3031.
67. (c) Gogoll, A.; Gomes, J.; Bergkvist, M.; Grennberg, H. Organometallics 1995, 14, 1354-1364.
68. (d) Consiglio, J. B.; Waymouth, R. W. Chem. Rev. 1989, 89, 257-276.
69. (e) Hansson, S.; Norrby, P. O.; Soegren, M. P. T.; Aakermark, B.; Cucciolito, M. E.; Giordano, F.; Vitagliano, A. Organometallics 1993, 12, 4940-4948.
70. (f) Faller, J. W.; Mattina, M. J. Inorg. Chem. 1972, 11, 1296-1307.
71. 2-allyl complexes: Clot, E.; Eisenstein, O.; Weng, T.-C.; Penner-Hahn, J.; Caulton, K. G. J. Am. Chem. Soc. 2004, 126, 9079-9084.
72. (a) Barloy, L.; Ramdeehul, S.; Osborn, J. A.; Carlotti, C.; Taulelle, F. ; De Cian, A.; Fischer, J. Eur. J. Inorg. Chem. 2000, 2523-2532.
73. (b) Ramdeehul, S.; Barloy, L.; Osborn, J. A. Organometallics 1996, 15, 5442-5444.
74. Braunstein, P.; Naud, F.; Dedieu, A.; Rohmer, M.-M.; DeCian, A.; Rettig, S. J. Organometallics 2001, 20, 2966-2981.
75. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, J. A., Jr.; Vreven, T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; Pople, J. A. Gaussian 03, revision C.02; Gaussian, Inc.: Wallingford, CT, 2004.
76. (a) Stephens, P. J.; Devlin, F. J.; Chabalowski, C. F.; Frisch, M. J. J. Phys. Chem. 1994, 98, 11623-11627.
77. (b) Kohn, W.; Becke, A. D.; Parr, R. G. J. Phys. Chem. 1996, 100, 12974-12980.
78. (c) Hay, P. J.; Wadt, W. R. J. Chem. Phys. 1985, 82, 270-283.
79. (d) Hay, P. J.; Wadt, W. R. J. Chem. Phys. 1985, 82, 284-298.
80. (e) Hay, P. J.; Wadt, W. R. J. Chem. Phys. 1985, 82, 299-310.
81. (a) Becke, A. D. J. Chem. Phys. 1993, 98, 5648-5653.
82. (b) Beeke, A. D. Phys. Rev. A 1988, 38, 3098-3100.
83. (c) Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785-789.
84. Sundermann, A.; Uzan, O.; Martin, J. M. L. Chem. Eur. J. 2001, 7, 1703-1711.
85. Bader, R. F. W. Atoms in Molecules. A Quantum Theory; Clarendon Press: Oxford, 1990.
86. Reed, A. E.; Curtiss, L. A.; Weinhold, F. Chem. Rev. 1988, 88, 899-926.
87. Woska, D.; Prock, A.; Giering, W. P. Organometallics 2000, 19, 4629-4638.
88. We did not locate a minimum corresponding to structure 13b. Activation of one of the P-H bonds to give a Pd hydride with a coordinated phosphide oxide is observed.
89. According to our previous calculations on similar systems at the same level (refs 17 and 39), this activation energy value can be easily surmounted.
90. Gómez-Bengoa, E.; Cuerva, J. M; Echavarren, A. M.; Martorell, G. Angew. Chem., Int. Ed. Engl. 1997, 36, 767-769.
91. Cárdenas, D. J.; Alcamí, M.; Cossío, F.; Méndez, M.; Echavarren, A. M. Chem. Eur. J. 2003, 9, 96-105.
92. A related process could be involved in Pd-catalyzed [3+2] intramolecular cycloadditions of alkenylidenecyclopropanes: (a) Gulías, M.; García, R.; Delgado, A.; Castedo, L.; Mascareñas, J. L. J. Am. Chem. Soc. 2006, 128, 384-385.
93. (b) Suzuki, T.; Fujimoto. H. Inorg. Chem. 2000, 39, 1113-1119.