Allylpalladium complexes with P-stereogenic monodentate phosphines. Application in the asymmetric hydrovinylation of styrene

Organometallics

Volumn 24, Issue 21, 2005, Pages 4961-4973

  Grabulosa, Arnald ^a   Müller, Guillermo ^a   Ordinas, Juan I ^a   Mezzetti, Antonio ^b   Maestro, Miguel Ángel ^c   Font Bardia, Mercè ^a   Solans, Xavier ^a  

^a UNIVERSITY OF BARCELONA   (Spain)

^b ETH ZURICH   (Switzerland)

^c UNIVERSITY OF A CORUÑA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

CODIMERIZATION; DOUBLE BONDS; PHOSPHINES; PHOSPHORUS ATOM;

BORON COMPOUNDS; COMPUTATIONAL GEOMETRY; COORDINATION REACTIONS; MOLECULAR STRUCTURE; PHOSPHATES; STEREOCHEMISTRY; SUBSTITUTION REACTIONS;

COMPLEXATION;

EID: 27144471465     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om050421v     Document Type: Article

References (112)

1. (a) Rajanbabu, T. V. Chem. Rev. 2003, 103, 2845.
2. (b) Jolly, P. W.; Wilke, G. In Applied Homogeneous Catalysis with Organometallic Compounds; Cornils, B., Herrmann, W. A., Eds.; VCH: New York, 2002; Vol. 3, p 1164.
3. (c) Goossen, L. J. Angew. Chem., Int. Ed. 2002, 41, 3775.
4. (a) Yi, C. S.; He, Z.; Lee, D. W. Organometallics 2001, 20, 802.
5. (b) He, Z.; Yi, C. S.; Donaldson, W. A. Org. Lett. 2003, 5, 1567.
6. (a) Boothe, U.; Rudbeck, H. C.; Tanner, D.; Johannsen, M. J. Chem. Soc., Perkin Trans. 1 2001, 3305.
7. (b) Dieno Buono, G.; Siv, C.; Peiffer, G.; Triantaphylides, C.; Denis, P.; Mortreux, A.; Petit, F. J. Org. Chem. 1985, 50, 1782.
8. (c) Hilt, G.; du Mesnil, F. X.; Lüers, S. Angew. Chem., Int. Ed. 2001, 40, 387.
9. (d) Kumareswaran, R.; Nandi, M.; Rajanbabu, T. V. Org. Lett. 2003, 5, 4345.
10. (e) Muller, G.; Ordinas, J. I. J. Mol. Catal. 1997, 125, 97.
11. (a) Britovsek, G. J. P.; Cavell, K. J.; Keim, W. J. Mol. Cotal. 1996, 110, 77.
12. (b) Nomura, N.; Jin, J.; Park, H.; RajanBabu, T. V. J. Am. Chem. Soc. 1998, 120, 459.
13. (c) Nandi, M.; Jin, J.; RajanBabu, T. V. J. Am. Chem. Soc. 1999, 121, 9899.
14. (d) Zhang, A.; RajanBabu, T. V. Org. Lett. 2004, 6, 1515.
15. (a) Wilke G., Angew. Chem., Int. Ed. Engl. 1988, 27, 185.
16. (b) Angerlund K., Eckerle A., Lutz F. Z. Naturforsch. 1995, 50b, 488.
17. Bayersdörfer, R.; Ganter, B.; Englert, U.; Keim, W.; Vogt, D. J. Organomet. Chem. 1998, 552, 187.
18. Gibson, S. E.; Ibrahim, H. Chem. Commun. 2002, 2465.
19. Park, H.; RajanBabu, T. V. J. Am. Chem. Soc. 2002, 124, 734.
20. Franciò, G.; Faraone, F.; Leitner, W. J. Am. Chem. Soc. 2002, 124, 736.
21. (a) RajanBabu, T. V.; Nomura, N.; Jin, J.; Radetich, B.; Park, H.; Nandi, M. Chem. Ear. J. 1999, 5, 1963.
22. (b) Rajanbabu, T. V.; Nomura, N.; Jin, J.; Nandi, M.; Park, H.; Sun, X. J. Org. Chem. 2003, 68, 8431.
23. (a) Hovestad, N. J.; Eggeling, E. B., Heidbüchel, H. J.; Jastrzebski, J. T. B. H.; Kragl, U.; Keim, W.; Vogt, D.; van Koten, G. Angew. Chem., Int. Ed. 1999, 38, 1655.
24. (b) Eggeling, E. V.; Hovestad, N. J.; Jastrzebski, J. T. B. H.; Vogt, D.; van Koten, G. J. Org. Chem. 2000, 65, 8857.
25. Benito, M.; Rossell, O.; Seco, M.; Muller, G.; Ordinas, J. L; Font-Bardia, M.; Solans, X. Eur. J. Inorg. Chem. 2002, 2477.
26. (a) Wegner, A.; Leitner, W. Chem. Commun. 1999, 1583.
27. (b) Bösmann, A.; Franciò, G.; Janssen, E.; Solinas, M.; Leitner, W.; Wasserscheid, P. Angew. Chem., Int. Ed. 2001, 40, 2697.
28. Ceder, R. M.; Muller, G.; Ordinas, J. I. J. Mol. Catal. 1994, 92, 127.
29. (a) Albert, J.; Cadena, J. M.; Graneil, J.; Muller, G.; Ordinas, J. I.; Panyella, D.; Puerta, C.; Sañudo, C.; Valerga, P. Organometallics 1999, 18, 3511.
30. (b) Albert, J.; Bosque, R.; Cadena, J. M.; Delgado, S.; Granell, J.; Muller, G.; Ordinas, J. I.; Font Bardia, M.; Solans, X. Chem. Eur. J. 2002, 8, 2279.
31. (a) Pietrusiewicz, K. M.; Zablocka, M. Chem. Rev. 1994, 94, 1375.
32. (b) Yamanoi, Y.; Imamoto, T. Rev. Heteroat. Chem. 1999, 20, 227.
33. (c) Ohff, M.; Holz, J.; Quirmbach, M.; Börner, A. Synthesis 1998, 1391.
34. (a) Horner, L.; Winkler, H.; Rapp, A.; Mentrup, A.; Hoffmann, H.; Beck, P. Tetrahedron Lett. 1961, 5, 161.
35. (b) Tani, K.; Brown, L. D.; Ahmed, J.; Ibers, J. A.; Yokota, M.; Nakamura, A.; Otsuka, S. J. Am. Chem. Soc. 1977, 99, 7876.
36. (c) Otsuka, S.; Nakamura, A.; Kano, T.; Tani, K. J. Am. Chem. Soc. 1971, 93, 4301.
37. (d) Wild, S. B. Coord. Chem. Rev. 1997, 166, 2291.
38. (e) Leung, P. H. Acc. Chem. Res. 2004, 37, 169.
39. (f) Lim, C.; Leung, P. H.; Sim, K. Y. Tetrahedron: Asymmetry 1994, 5, 1883.
40. (g) Liu, A.; Mok, K. F.; Leung, P. H. Chem. Commun. 1997, 2397.
41. (h) He, G.; Mok, K. F.; Leung, P. H. Organometallics 1999, 18, 4027.
42. (i) Gladiali, S.; Dore, A.; Fabbri, D.; De Lucchi, O.; Manassero, M. Tetrahedron: Asymmetry 1994,5, 511.
43. (j) Fabel, M.; Willis, A. C.; Wild, S. B. Angew. Chem., Int. Ed. Engl. 1994, 33, 1835.
44. (k) Dunina, V. V.; Golovan, E. B. Tetrahedron: Asymmetry 1995, 6, 2747.
45. (l) Dunina, V. V.; Kuzmina, L. G.; Rubina, M. Y.; Grishin. Y. K.; Veits, Y. A.; Kazakova, E. I. Tetrahedron: Asymmetry 1999, 10, 1483.
46. (m) Albert, J.; Granell, J.; Mínguez, J.; Muller, G.; Sainz, D.; Valerga, P. Organometallics 1997, 16, 3561.
47. Moncarz, J. R.; Brunker, T. J.; Glueck, D. S.; Sommer, R. D.; Rheingold, A. L. J. Am. Chem. Soc. 2003, 125, 1180.
48. (a) Imamoto, T.; Oshiki, T.; Onozawa, T.; Kusumoto, T.; Sato, K. J. Am. Chem. Soc. 1990, 112, 5244.
49. (b) Watanabe, T.; Gridnev, I. D.; Imamoto, T. Chirality 2000, 12, 346.
50. (c) Koide, Y.; Sakamoto, A. T.; Imamoto, T. Tetrahedron Lett. 1991, 28, 3375.
51. (a) Imamoto, T.; Watanabe, J.; Wada, Y.; Masuda, H.; Yamada, H.; Tsuruta, H.; Matsukawa, S.; Yamaguchi, K. J. Am. Chem. Soc. 1998, 120, 1635.
52. (b) Gridnev, I. D.; Higashi, N.; Imamoto, T. Organometallics 2001, 20, 4542.
53. (c) Oohara, N.; Katagiri, K; Imamoto, T. Tetrahedron: Asymmetry 2003, 14, 2171.
54. Wolfe, B.; Livinghouse, T. J. Am. Chem. Soc. 1998, 120, 5116.
55. (a) Jugé, S.; Genet, J. P. Tetrahedron Lett. 1989, 21, 2783.
56. (b) Jugé, S.; Stephan, M.; Lafitte, J. A.; Genet, J. P. Tetrahedron Lett. 1990, 31, 6357.
57. (c) Jugé, S.; Stephan, M.; Merdès, R.; Genet, J. P.; Halut-Desportes, S. Chem. Commun. 1993, 531.
58. (d) Moulin, D.; Bago, S.; Bauduin, C.; Darcel, C.; Jugé, S. Tetrahedron: Asymmetry 2000, 11, 3939.
59. (e) Moulin, D.; Darcel, C.; Jugé, S. Tetrahedron: Asymmetry 1999, 10, 4729.
60. (f) Moulin, D.; Bago, S.; Bauduin, C.; Darcel, C.; Jugé, S. Tetrahedron: Asymmetry 2000, 11, 3939.
61. (a) Jugé, S.; Genet, J. P. Tetrahedron Lett. 1989, 30, 2783.
62. (b) Andersen, N. G.; Ramsden, P. D.; Che, D.; Parvez, M.; Keay, B. A. J. Org. Chem. 2001, 66, 7478.
63. (a) Nettekoven, U.; Kamer, P. C. J.; Widhalm, M.; van Leeuwen, P. W. N. M. Organometallics 2000, 19, 4596.
64. (b) Nettekoven, U.; Widhalm, M.; Kamer, P. C. J.; van Leeuwen, P. W. N. M.; Mereitner, K.; Lutz, M.; Spek, A. L. Organometallics 2000, 19, 2299.
65. (c) Nettekoven, U.; Widhalm, M.; Kalchhauser, H.; Kamer, P. C. J.; van Leeuwen, P. W. N. M.; Lutz, M.; Spek, A. L. J. Org. Chem. 2001, 66, 759.
66. (d) Brown, J. M.; Laing, J. C. P. J. Organomet. Chem. 1997, 529, 435.
67. (e) Maienza, F.; Wörle, H.; Steffanut, P.; Mezzetti, A.; Spindler, F. Organometallics 1999, 18, 1041.
68. (f) Colby, E. A.; Jamison, T. F. J. Org. Chem. 2003, 68, 156.
69. Richter, W. J. Chem. Ber. 1984, 117, 2328.
70. Rippert, A. J.; Linden, A.; Hansen, H. J. Helv. Chim. Acta 2000, 83, 311.
71. (a) Bauduin, C.; Moulin, D.; Kaloun, E. B.; Darcel, C.; Jugé, S. J. Org. Chem. 2003, 68, 4293.
72. (b) Humbel, S.; Bertrand, C.; Darcel, C.; Bauduin, C.; Jugé, S. Inorg. Chem. 2003, 42, 420.
73. (a) Stoop, R. M.; Mezzetti, A.; Spindler, F. Organometallics 1998, 17, 668.
74. (b) Tsuruta, H.; Imamoto, T. Synlett 2001, 999.
75. (c) Pescher, P.; Caude, M.; Rosset, R.; Tambuté, A.; Oliveros, L. Nouv. J. Chim. 1985, 9, 621.
76. (a) Nagata, K.; Matsukawa, S.; Imamoto, T. J. Org. Chem. 2000, 65, 4185.
77. (b) Vedejs, E.; Donde, Y. J. Org. Chem. 2000, 65, 2337.
78. (a) Kawatsura, M.; Uozumi, Y.; Hayashi, T. Chem. Commun. 1998, 217.
79. (b) Mandal, S. K.; Gowda, G. A. N.; Krishnamurthy, S. K.; Zheng, C.; Li, S.; Hosmane, N. S. J. Organomet. Chem. 2003, 676, 22.
80. (c) Boele, M. D. K.; Kamer, P. C. J.; Lutz, M.; Spek, A. L.; de Vries, J. G.; Leeuwen, P. W. N. M.; van Strijdonck, G. P. F. Chem. Eur. J. 2004, 10, 6232.
81. Kollmar, M.; Steinhagen, H.; Janssen, J. P.; Goldfuss, B.; Malinovskaya, S. A.; Vázquez, J.; Rominger, F.; Helmchen, G. Chem. Eur. J. 2002, 8, 310.
82. (a) Åkermark. B.; Krakenberger, B.; Hansson, S.; Vitagliano, A. Organometallics 1987, 6, 620.
83. (b) Kumar, P. G. A.; Dotta, P.; Hermatschweiler, R.; Pregosin, P. S.; Albinati, A.; Rizzato, S. Organometallics 2005, 24, 1306.
84. Boele, M. D. K.; Kamer, P. C. J.; Lutz, M.; Spek, A. L.; de Vries, J. G.; van Leeuwen, P. W. N. M.; van Strijdonck, G. P. F. Chem. Eur. J. 2004, 10, 6232.
85. (a) Andrieu, J.; Camus, J. M.; Dietz, J.; Richard, P.; Poli, R. Inorg. Chem. 2001, 40, 1597.
86. (b) Leznoff, D. B.; Rancurel, C.; Sutter, J. P.; Rettig, S. J.; Pink, M.; Kahn, O. Organometallics 1999, 18, 5097.
87. Faller, J. W.; Sarantopoulos, N. Organometallics 2004, 23, 2008.
88. (a) Englert, U.; Haerter, R.; Vasen, D.; Salzer, A.; Eggeling, E. B.; Vogt, D. Organometallics 1999, 18, 4390.
89. (b) Shi, W. J.; Xie, J. H.; Zhou, Q. L. Tetrahedron: Asymmetry 2005, 16, 705.
90. Faissner, R.; Huttner, G. Eur. J. Inorg. Chem. 2003, 2239.
91. (a) Faller, J. W.; Sarantopoulos, N. Organometallics 2004, 23, 2008.
92. (b) Dotta, P.; Kumar, P. G. A.; Pregosin, P. S.; Albinati, A. Helv. Chim. Acta 2004, 87, 272.
93. Ceder, R. M.; García, C.; Muller, G.; Rocamora, M. Manuscript in preparation.
94. Maruyama K.; Kuroki T.; Mizoroki T.; Ozaki A. Bull. Chem. Soc. Jpn. 1971, 44, 2002.
95. Kawakami, K.; Kawata, N.; Maruya, K.; Mizoroki, T.; Ozaki, A. J. Catal. 1975, 39, 134.
96. (a) Mann, B. E.; Shaw, S. D. J. Organomet. Chem. 1987, 326, C13.
97. (b) Mann, B. E.; Keasey, A.; Sonoda, A.; Maitlis, P. M. J. Chem. Soc., Dalton Trans. 1979, 338.
98. Cárdenas, D. J.; Alcamí, M.; Cossió, F.; Méndez, M.; Echavarren, A. M. Chem. Eur. J. 2003, 9, 96.
99. Nettekoven, U.; Hartwig, J. F. J. Am. Chem. Soc. 2002, 124, 1166.
100. Gatti, G.; Lopez, J. A.; Mealli, C.; Musco, A. J. Organomet. Chem. 1994, 483, 77.
101. Rix, F. C.; Brookhart, M.; White, P. S. J. Am. Chem. Soc. 1996, 118, 2436.
102. Crascall, L. E.; Litster, S. A.; Redhouse, A. D.; Spencer, J. L. J. Organomet. Chem. 1990, 394, C35.
103. Crascall, L. E.; Spencer, J. L. Dalton Trans. 1992, 3445.
104. Hölscher, M.; Franciò, G.; Leitner, W. Organometallics 2004, 23, 5606.
105. Dent, W. T.; Long, R.; Wilkinson, A. J. J. Chem. Soc. 1964, 1585.
106. Auburn, P.; Mackenzie, P. B.; Bosnich, B. J. Am. Chem. Soc. 1985, 107, 2033.
107. (a) Sheldrick, G. M. SHELXS 97: A Computer Program for Crystal Structure Determination; University of Göttingen: Germany, 1997.
108. (b) Sheldrick, G. M. SHELXL 97: A Computer Program for Crystal Structure Refinement; University of Göttingen: Germay, 1997.
109. Sheldrick, G. M. SADABS: A Program for Empirical Absorption Correction of Area Detector Data; University of Göttingen: Germany, 1996.
110. Based on the method of Robert Blessing: Blessing, R. H. Acta Crystallogr. 1995, A51, 33.
111. (a) Lardicci, L.; Salvadori, P.; Caporusso, A. M.; Menicagli, R.; Belgodere, E. Gazz. Chim. Ital. 1972, 102, 64.
112. (b) Menicagli, R.; Piccolo, O.; Lardicci, L.; Wis, M. L. Tetrahedron 1979, 35, 1301.