Palladium complexes of bulky ortho-trifluoromethylphenyl-substituted phosphines: Unusually regioselective catalysts for the hydroxycarbonylation and alkoxycarbonylation of alkenes

Journal of Molecular Catalysis A: Chemical

Volumn 330, Issue 1-2, 2010, Pages 18-25

  Grabulosa, Arnald ^a   Frew, Jamie J R ^a   Fuentes, José A ^a   Slawin, Alexandra M Z ^a   Clarke, Matthew L ^a  

^a UNIVERSITY OF ST ANDREWS   (United Kingdom)

Author keywords

Hydrocarbonylation; Hydroesterification; Hydroxycarbonylation; Palladium; Suzuki coupling

Indexed keywords

ALKOXYCARBONYLATION; ARYL CHLORIDE; CO CATALYSTS; CONE ANGLE; COORDINATION ABILITY; ELECTRONIC EFFECTS; HYDROCARBONYLATION; HYDROESTERIFICATION; HYDROXYCARBONYLATION; LITHIUM CHLORIDE; N-PROPANOL; PALLADIUM COMPLEXES; PD COMPLEX; PHOSPHINE LIGANDS; PRECATALYSTS; REGIO-SELECTIVE; SUZUKI COUPLINGS; SUZUKI REACTION; TRIPHENYL PHOSPHINES;

CARBONYLATION; CATALYSTS; CHLORINE COMPOUNDS; ETHANOL; LIGANDS; LITHIUM; OLEFINS; PALLADIUM; PHOSPHORUS COMPOUNDS; REGIOSELECTIVITY; SEMICONDUCTING INDIUM GALLIUM ARSENIDE; STYRENE; X RAY CRYSTALLOGRAPHY;

PALLADIUM COMPOUNDS;

EID: 77956708692     PISSN: 13811169     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.molcata.2010.06.026     Document Type: Article

References (40)

1. Some selected examples of the advantageous use of bulky phosphines in various types of carbonylation reactions: B. Breit, and E. Fuchs Chem. Commun. 2004 694
2. M.L. Clarke, and G.J. Roff Chem. Eur. J. 12 2006 7978
3. M.L. Clarke, and G.J. Roff Green Chem. 9 2007 792
4. B. Breit, R. Winde, T. Mackewitz, R. Paciello, and K. Harms Chem. Eur. J. 7 2001 3106
5. A. van Rooy, E.N. Orij, P.C.J. Kamer, and P.W.N.M. van Leeuwen Organometallics 14 1995 34
6. R.A. Baber, M.L. Clarke, K. Heslop, A. Marr, A.G. Orpen, P.G. Pringle, A.M. Ward, and D.A. Zambrano-Williams Dalton Trans. 2005 1079
7. P.S. Bäuerleina, I.A. Gonzaleza, J.J.M. Weemersa, M. Lutz, A.L. Spek, D. Vogt, and C. Müller Chem. Commun. 2009 4944
8. M. Dieguez, O. Pamies, A. Ruiz, S. Castillon, and C. Claver Chem. Eur. J. 7 2001 3086
9. C.J. Cobley, J. Klosin, C. Qin, and G.T. Whiteker Org. Lett. 6 2004 3277
10. P.W.N.M. Van Leeuwen, and C. Claver Rhodium Catalysed Hydroformylation 2000 Kluwer Academic Publishers Dordrecht
11. M.L. Clarke Curr. Org. Chem. 9 2005 701
12. B. Breit, and W. Seiche Synthesis 2001 1
13. J. Klosin, and C.R. Landis Acc. Chem. Res. 40 2007 1251
14. R.I. Pugh, E. Drent, and P.G. Pringle Chem Commun. 2001 1476
15. C.J. Rodriguez, D.F. Foster, G.R. Eastham, and D.J. Cole-Hamilton Chem. Commun. 2004 1720
16. W. Clegg, G.R. Eastham, M.R.J. Elsegood, R.P. Tooze, X.L. Wang, and K. Whiston Chem. Commun. 1999 1877
17. J.J.R. Frew, M.L. Clarke, U. Meyer, H. Van Rensburg, and R.P. Tooze Dalton Trans. 2008 1976
18. J.J.R. Frew, K. Damian, H. Van Rensburg, A.M.Z. Slawin, R.P. Tooze, M.L. Clarke, and R.P. Tooze Chem. Eur. J. 15 2009 10504
19. I. del Rio, N. Ruiz, C. Claver, L.A. van der Veen, and P.W.N.M. van Leeuwen J. Mol. Catal. A: Chem. 161 2000 39
20. ortho-Trifluomethylphenyl phosphines are quite sparsely studied phosphines in any case, most likely due to their steric bulk hindering their ability to act as ligands. B. Croxtall, J. Fawcett, E.G. Hope, and A.M. Stuart Dalton Trans. 2002 491
21. S. Jääskeläinen, P. Suomalainan, M. Haukka, H. Riihimäki, J.T. Pursiainen, and T.A. Pakkanen J. Organomet. Chem. 633 2001 69
22. M.L. Clarke, D. Elliss, K.L. Mason, A.G. Orpen, P.G. Pringle, R. Wingad, and D.A. Zaheer Dalton Trans. 2005 1294
23. C.A. Tolman Chem. Rev. 77 1977 313
24. I. del Rio, C. Claver, and P.W.N.M. van Leeuwen Eur. J. Inorg. Chem. 2001 2719
25. For a review on industrial use of Pd catalysts including Naproxen synthesis. A. Zapf, and M. Beller Top. Catal. 19 2002 101
26. S. Jayasree, A. Seayad, and R.V. Chaudhari Chem. Commun. 2000 1239
27. A. Seayad, S. Jayasree, and R.V. Chaudhari Org. Lett. 1 1999 459
28. M.S. Goedheijt, J.N.H. Reek, P.C.J. Kamer, and P.W.N.M. Van Leeuwen Chem. Commun. 1998 2431
29. A chiral phosphonic acid additive was communicated to give very good e.e. in hydroxycarbonylation, but unfortunately yields were moderate and over 10% catalyst was required. H. Alper, and N. Hamel J. Am. Chem. Soc. 112 1990 2803
30. A. Ionescu, G. Laurenczy, and O.F. Wendt Dalton Trans. 2006 3934
31. A. Aghmiz, M. Gimenez-Pedris, A.M. Masdeu-Bulto, and F.P. Schmidtchen Catal. Lett. 103 2005 191
32. A. Ionescu, M. Ruppel, and O.F. Wendt J. Organomet. Chem. 691 2006 3806
33. Selected references of alkoxycarbonylation: E. Guiu, M. Caporali, B. Munoz, C. Muller, M. Lutz, A.L. Spek, C. Claver, and P.W.N.M. Van Leeuwen Organometallics 25 2006 3102
34. C. Goddard, A. Ruiz, and C. Claver Helv. Chim. Acta 89 2006 1610
35. B. Munoz, A. Marinetti, A. Ruiz, S. Castillon, and C. Claver Inorg. Chem. Commun. 8 2005 1113
36. S. Oi, M. Nomura, T. Aiko, and Y. Inoue J. Mol. Catal. A 115 1997 289
37. G. Cometti, and G.P. Chiousoli J. Organomet. Chem. 236 1982 C31
38. D.B.G. Williams, M.L. Shaw, M.J. Green, and C.W. Holzapfel Angew. Chem. Int. Ed. 47 2008 560
39. L.L. Da Rocha, A. de, O. Dias, E.N. dos Santos, R. Augusti, and E. Gusevskaya J. Mol. Catal. Sect. A 132 1998 213
40. H. Ooka, T. Innoue, S. Itsuno, and M. Tanaka Chem. Commun. 2005 1173