Methoxycarbonylation of styrene to methyl arylpropanoates catalyzed by palladium(II) precursors with 1,1′-bis(diphenylphosphino)metallocenes

Journal of Molecular Catalysis A: Chemical

Volumn 224, Issue 1-2, 2004, Pages 35-49

  Bianchini, Claudio ^a   Meli, Andrea ^a   Oberhauser, Werner ^a   Parisel, Sebastien ^a   Gusev, Oleg V ^b   Kal'sin, Alexander M ^b   Vologdin, Nikolai V ^b   Dolgushin, Fedor M ^b  

^a ICCOM CNR   (Italy)

^b A N NESMEYANOV INSTITUTE OF ORGANOELEMENT COMPOUNDS   (Russian Federation)

Author keywords

1,1 Bis(diphenylphosphino)metallocenes; Alkoxycarbonylation; Alkyl arylpropanoates; Palladium; Regioselectivity

Indexed keywords

LINEAR ISOMERS; METHOXYCARBONYLATION; OSMOCENE;

CARBONYLATION; COMPLEXATION; ISOMERS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION KINETICS; RUTHENIUM COMPOUNDS; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL);

CATALYSIS;

1,1' BIS(DIPHENYLPHOSPHINO)FERROCENE; 1,1' BIS(DIPHENYLPHOSPHINO)OCTAMETHYLFERROCENE; 1,1' BIS(DIPHENYLPHOSPHINO)OSMOCENE; 1,1' BIS(DIPHENYLPHOSPHINO)RUTHENOCENE; 4 PHENYLPROPANOATE; ALKENE DERIVATIVE; BENZENE DERIVATIVE; FERROCENE DERIVATIVE; METHYL GROUP; PALLADIUM COMPLEX; PHOSPHORUS DERIVATIVE; RUTHENOCENE DERIVATIVE; STYRENE; SULFONIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CARBONYLATION; CATALYSIS; CATALYST; ISOMER; METHOXYCARBONYLATION; NUCLEAR MAGNETIC RESONANCE; PRESSURE; STEREOCHEMISTRY; SYNTHESIS;

EID: 9144242766     PISSN: 13811169     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.molcata.2004.06.029     Document Type: Article

References (82)

1. T.J. Colacot Platinum Met. Rev. 45 2001 22
2. K.S. Gan, and T.S.A. Hor A. Togni T. Hayashi Ferrocenes: Homogeneous Catalysis, Organic Synthesis, Materials Science 1995 VCH/Wiley Weinheim 13 Chapter 1
3. S. Li, B. Wei, P.M.N. Low, H.K. Lee, T.S.A. Hor, F. Xue, and T.C.W. Mak J. Chem. Soc., Dalton Trans. 1997 1289
4. J.M. Brown, and P.J. Guiry Inorg. Chim. Acta 220 1994 149
5. M. Ogasawara, K. Yoshida, and T. Hayashi Organometallics 19 2000 1567
6. B.E. Bosch, I. Brümmer, K. Kunz, G. Erker, R. Frölich, and S. Kotila Organometallics 19 2000 1255
7. Y. Xie, G.K. Tan, Y.K. Yan, J.J. Vittal, S.C. Ng, and T.S.A. Hor J. Chem. Soc., Dalton Trans. 1999 773
8. S.W.A. Fong, and T.S.A. Hor J. Cluster Sci. 9 1998 351
9. T. Hayashi, M. Konishi, Y. Kobori, M. Kumada, T. Higuchi, and K. Hirotsu J. Am. Chem. Soc. 106 1984 158
10. A. Jutand, A.K.-K. Mimi Hii, M. Thornton-Pett, and J.M. Brown Organometallics 18 1999 5367
11. A.L. Boyes, I.R. Butler, and S.C. Quayle Tetrahedron Lett. 39 1998 7763
12. J.M. Brown, and K.-K. Mimi Hii Angew. Chem. Int. Ed. 35 1996 657
13. W. Mägerlein, A.F. Indolese, M. Beller, and M. Angew Chem. Int. Ed. 40 2001 2856
14. J.F. Hartwig Angew. Chem. Int. Ed. 37 1998 2090
15. J.F. Hartwig Acc. Chem. Res. 31 1998 852
16. M.S. Driver, and J.F. Hartwig J. Am. Chem. Soc. 118 1996 7217
17. K. Li, P.N. Horton, M.B. Hursthouse, and K.-K. Mimi Hii J. Organomet. Chem. 665 2003 250
18. T.E. Müller, M. Berger, M. Grosche, E. Herdtweck, and F.P. Schmidtchen Organometallics 20 2001 4384
19. K. Mikami, and K. Aikawa Org. Lett. 4 2002 99
20. C. Bianchini, A. Meli, W. Oberhauser, P.W.N.M. van Leeuwen, M.A. Zuideveld, Z. Freixa, P.C.J. Kamer, A.L. Spek, O.V. Gusev, and A.M. Kal'sin Organometallics 22 2003 2409
21. O.V. Gusev, A.M. Kal'sin, M.G. Peterleitner, P.V. Petrovskii, K.A. Lyssenko, N.G. Akhmedov, C. Bianchini, A. Meli, and W. Oberhauser Organometallics 21 2002 3637
22. M.A. Zuideveld, P.C.J. Kamer, P.W.N.M. van Leeuwen, P.A.A. Klusener, H.A. Stil, and C.F. Roobeek J. Am. Chem. Soc. 120 1998 7977
23. O.V. Gusev, private communication.
24. O.V. Gusev, A.M. Kal'sin, P.V. Petrovskii, K.A. Lyssenko, Y.F. Oprunenko, C. Bianchini, A. Meli, and W. Oberhauser Organometallics 22 2003 913
25. D. Drew, and J.R. Doyle Inorg. Synth. 13 1972 47
26. R.E. Rülke, J.M. Ernsting, A.L. Spek, C.J. Elsevier, P.W.N.M. van Leeuwen, and K. Vrieze Inorg. Chem. 32 1993 5769
27. F. Gorla, and L.M. Venanzi Helv. Chim. Acta 73 1990 690
28. C. Benettolo, R. Bertani, G. Bombieri, and L. Toniolo Inorg. Chim. Acta 233 1995 5
29. P.J. Stang, D.H. Cao, G.T. Poulter, and A.M. Arif Organometallics 14 1995 1110
30. W.J. Geary Coord. Chem. Rev. 7 1971 81
31. R. Morassi, and L. Sacconi J. Chem. Soc. A 1971 492
32. C. Bianchini, A. Meli, A. Traversi, Italian Patent FI A000025 (1997).
33. A.J.C. Wilson International Tables for X-ray Crystallography 1992 Kluwer Dordrecht, The Netherlands p. 219
34. A.J.C. Wilson International Tables for X-ray Crystallography 1992 Kluwer Dordrecht, The Netherlands p. 500
35. C. Nataro, A.N. Campbell, M.A. Ferguson, C.D. Incarvito, and A.L. Rheingold J. Organomet. Chem. 673 2003 47
36. M. Sato, H. Shigeta, M. Sekino, and S. Akabori J. Organomet. Chem. 458 1993 199
37. M. Portnoy, and D. Milstein Organometallics 13 1994 600
38. M. Portnoy, F. Frolow, and D. Milstein Organometallics 10 1991 3960
39. I. Toth, and C.J. Elsevier Organometallics 13 1994 2118
40. P.H.M. Budzelaar, P.W.N.M. van Leeuwen, and C.F. Roobeek Organometallics 11 1992 23
41. A. Hohn B. Cornils W.A. Hermann Applied Homogeneous Catalysis with Organometallic Compounds 1996 VCH Weinheim 138
42. M. Beller, and A.M. Tafesh B. Cornils W.A. Hermann Applied Homogeneous Catalysis with Organometallics Compounds 1996 VCH Weinheim 187
43. E. Drent, and P.H.M. Budzelaar J. Organomet. Chem. 593-594 2000 211
44. A. Seayad, S. Jayasree, K. Damodaran, L. Toniolo, and R.V. Chaudhari J. Organomet. Chem. 601 2000 100
45. A. Seayad, A.A. Kelkar, L. Toniolo, and R.V. Chaudhari J. Mol. Catal. A 151 2000 47
46. I. Del Rio, N. Ruiz, C. Claver, L.A. van der Veen, and P.W.N.M. van Leeuwen J. Mol. Catal. A 161 2000 39
47. S. Oi, M. Nomura, T. Aiko, and Y. Inoue J. Mol. Catal. A 115 1997 289
48. P.J. Perez, J.C. Calabrese, and E.E. Bunel Organometallics 20 2001 337
49. A. Sen Acc. Chem. Res. 26 1993 303
50. E. Drent, and P.H.M. Budzelaar Chem. Rev. 96 1996 663
51. E. Drent, J.A.M. van Broekhoven, and P.H.M. Budzelaar B. Cornils W.A. Hermann Applied Homogeneous Catalysis with Organometallic Compounds 1996 VCH Weinheim 333
52. A. Sommazzi, and F. Garbassi Prog. Polym. Sci. 22 1997 1547
53. K. Nozaki, and T. Hijama J. Organomet. Chem. 576 1999 248
54. C. Bianchini, and A. Meli Coord. Chem. Rev. 225 2002 35
55. E. Drent, J.A.M. van Broekhoven, and P.H.M. Budzelaar B. Cornils W.A. Hermann Applied Homogeneous Catalysis with Organometallic Compounds 1996 VCH Weinheim 344
56. R.A.M. Robertson, and D.J.C. Cole-Hamilton Coord. Chem. Rev. 225 2002 67
57. C. Bianchini, A. Meli, and W. Oberhauser J. Chem. Soc., Dalton Trans. 2003 2627
58. C. Bianchini, G. Mantovani, A. Meli, W. Oberhauser, P. Bruggeller, and T. Stampfl J. Chem. Soc., Dalton Trans. 2001 690
59. M. Sperrle, and G. Consiglio J. Mol. Catal. A 143 1999 263
60. M. Sperrle, and G. Consiglio Chem. Ber. 130 1997 1557
61. M. Sperrle, and G. Consiglio J. Organomet. Chem. 506 1996 177
62. G. Consiglio, S.C.A. Nefkens, and C. Pisano Inorg. Chim. Acta 220 1994 273
63. C. Pisano, and G. Consiglio Gazz. Chim. Ital. 124 1994 393
64. C. Pisano, A. Mezzetti, and G. Consiglio Organometallics 11 1992 20
65. C. Pisano, C.A. Nefkens, and G. Consiglio Organometallics 11 1992 1975
66. C. Pisano, G. Consiglio, A. Sironi, and M. Moret J. Chem. Soc., Chem. Commun. 1991 421
67. M. Barsaccchi, G. Consiglio, L. Medici, G. Petrucci, and U.W. Suter Angew. Chem. Int. Ed. Engl. 30 1991 989
68. R.P. Tooze, K. Whiston, A.P. Molyan, M.J. Taylor, and N.W. Wilson J. Chem. Soc., Dalton Trans. 2000 3441
69. C. Bianchini, A. Meli, G. Müller, W. Oberhauser, and E. Passaglia Organometallics 21 2002 4965
70. C. Bianchini, H.M. Lee, A. Meli, W. Oberhauser, M. Peruzzini, and F. Vizza Organometallics 21 2002 16
71. C. Bianchini, H.M. Lee, A. Meli, S. Moneti, F. Vizza, M. Fontani, and P. Zanello Macromolecules 32 1999 4183
72. L.M. Engelhardt, J.M. Patrick, C.L. Raston, P. Twiss, and A.H. White Aust. J. Chem. 37 1984 2193
73. A. Aeby, and G. Consiglio J. Am. Chem. Soc. 120 1998 11000
74. K. Nozaki, H. Komaki, Y. Kawashima, T. Hiyama, and T. Matsubara J. Am. Chem. Soc. 123 2001 534
75. M.A. Zuideveld, B.H.G. Swennenhuis, P.C.J. Kamer, and P.W.N.M. van Leeuwen J. Organomet. Chem. 637 2001 805
76. M.A. Zuideveld, B.H.G. Swennenhuis, M.D.K. Boele, Y. Guari Y., G.P.F. van Strijdonck, J.N.H. Reek, P.C.J. Kamer, K. Goubitz, J. Fraanje, M. Lutz, A.L. Spek, and P.W.N.M. van Leeuwen J. Chem. Soc., Dalton Trans. 2002 2308
77. P.W.N.M. van Leeuwen, M.A. Zuideveld, B.H.G. Swennenhuis, Z. Freixa, P.C.J. Kamer, K. Goubitz, J. Fraanje, M. Lutz, and A.L. Spek J. Am. Chem. Soc. 125 2003 5523
78. Y. BeCker, and J.K. Stille J. Am. Chem. Soc. 100 1978 845
79. J.S. Roberts, and K.J. Klabunde J. Am. Chem. Soc. 99 1977 2509
80. G. Cavinato, and L. Toniolo J. Mol. Catal. 10 1981 161
81. B. Jedlicka, W. Weissensteiner, T. Kegl, and L. Kollar J. Organomet. Chem. 563 1998 37
82. G.P.C.M. Dekker, C.J. Elsevier, K. Vrieze, P.W.N.M. van Leeuwen, and C.F. Roobeek J. Organomet. Chem. 430 1992 357