Palladium(0) complexes with unsymmetric bidentate nitrogen ligands for the stereoselective hydrogenation of 1-phenyl-1-propyne to (Z)-1-phenyl-1-propene

Organometallics

Volumn 21, Issue 8, 2002, Pages 1546-1553

  Van Laren, Martijn W ^a   Duin, Marcel A ^a   Klerk, Chantal ^a   Naglia, Michele ^a,b   Rogolino, Dominga ^a,b   Pelagatti, Paolo ^b   Bacchi, Alessia ^b   Pelizzi, Corrado ^b   Elsevier, Cornelis J ^a  

^a UNIVERSITY OF AMSTERDAM   (Netherlands)

^b UNIVERSITY OF PARMA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSTS; COMPLEXATION; HYDROCARBONS; HYDROGENATION; PALLADIUM COMPOUNDS; SUBSTITUTION REACTIONS; X RAY ANALYSIS;

STEREOSELECTIVE HYDROGENATION;

ORGANOMETALLICS;

EID: 0012397516     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om0108346     Document Type: Article

References (49)

1. For example: Collman, J. P. Hegedus, L. S. Norton, J. R. Finke, R. G. Principles and Applications of Organotransition Metal Chemistry; University Science Books: Mill Valley, CA, 1987.
2. Knowles, W. S. Acc. Chem. Res. 1983, 16, 106.
3. (b) Mashima, K. Kusano, K. Ohta, T. Notori, R. Takaya, H. J. Chem. Soc., Chem. Commun. 1989, 1208.
4. (a) Lindlar, H. Helv. Chim. Acta 1952, 35, 446.
5. (b) Lindlar, H. Dubuis, R. Org. Synth. 1966, 46, 89.
6. Choi, J. Yoon, N. M. Tetrahedron Lett. 1996, 37, 1037.
7. (a) Brown, C. A. Ahuja, V. K. J. Chem. Soc., Chem. Commun. 1973, 553.
8. (b) Brown, C. A. Ahuja, V. K. J. Org. Chem. 1973, 38, 2226.
9. Schrock, R. R. Osborn, J. A. J. Am. Chem. Soc. 1976, 98, 2143.
10. Sodeoka, M. Shibasaki, M. J. Org. Chem. 1985, 50, 1147.
11. van Laren, M. W. Elsevier, C. J. Angew. Chem., Int. Ed. 1999, 38, 3715.
12. (a) van Asselt, R. Elsevier, C. J. Spek, A. L. Benedix, R. Recl. Trav. Chim. Pays-Bas 1994, 113, 88.
13. (b) van Asselt, R. Elsevier, C. J. Smeets, W. J. J. Spek, A. L. Inorg. Chem. 1994, 33, 1521.
14. van Asselt, R. Elsevier, C. J. J. Mol. Catal. 1991, 65, L13.
15. (a) van Asselt, R. Elsevier, C. J. Organometallics 1992, 11, 1999.
16. (b) van Asselt, R. Elsevier, C. J. Tetrahedron 1994, 50, 323.
17. (c) van Belzen, R. Elsevier, C. J. Angew. Chem., Int. Ed. Engl. 1997, 36, 1743.
18. (d) van Belzen, R. Klein, R. A. Kooijman, H. Veldman, N. Spek, A. L. Elsevier, C. J. Organometallics 1998, 17, 1812.
19. (e) Elsevier, C. J. Coord. Chem. Rev. 1999, 185-186, 809.
20. (a) Bacchi, A. Carcelli, M. Costa, M. Pelagatti, P. Pelizzi, C. Pelizzi, G. Gazz. Chim. Ital. 1994, 124, 429.
21. (b) Bacchi, A. Carcelli, M. Costa, M. Leporati, A. Leporati, E. Pelagatti, P. Pelizzi, C. Pelizzi, G. J. Organomet. Chem. 1997, 535, 107.
22. (c) Pelagatti, P. Venturing A. Leporati, A. Carcelli, M. Costa, M. Bacchi, A. Pellizi, G. Pelizzi, C. J. Chem. Soc., Dalton Trans. 1998, 2715.
23. Pelagatti, P. Bacchi, A. Carcelli, M. Costa, M. Fochi, A. Ghidini, P. Leporati, E. Masi, M. Pelizzi, C. Pelizzi, G. J. Organomet. Chem. 1999, 583, 94.
24. (a) Canovese, L. Visentin, F. Uguagliati, P. Crociani, B. Di Bianca, F. Inorg. Chim. Acta 1995, 235, 45.
25. (b) Crociani, B. Antonaroli, S. Di Bianca, F. Canovese, L. Visentin, F. Uguagliati, P. J. Chem. Soc., Dalton Trans. 1994, 1145.
26. (a) Crociani, B. Di Bianca, F. Canovese, L. Uguagliati, P. J. Organomet. Chem. 1990, 381, C17.
27. (b) Crociani, B. Di Bianca, F. Uguagliati, P. Canovese, L. Berton, A. J. Chem. Soc., Dalton Trans. 1991, 71.
28. (c) Crociani, B. Antonaroli, S. Di Bianca, F. Fontana, A. J. Organomet. Chem. 1993, 450, 21.
29. Canovese, L. Visentin, F. Uguagliati, P. Crociani, B. J. Chem. Soc., Dalton Trans. 1996, 1921.
30. Borriello, C. Ferrara, M. L. Orabona, I. Panunzi, A. Ruffo, F. J. Chem. Soc., Dalton Trans. 2000, 2545.
31. Rülke, R. E. Delis, J. G. P. Groot, A. M. Elsevier, C. J. van Leeuwen, P. W. N. M. Vrieze, K. Goubitz, K. Schenk, H. J. Organomet. Chem. 1996, 508, 109.
32. Groen, J. H. Vlaar, M. J. M. van Leeuwen, P. W. N. M. Vrieze, K. Kooijman, H. Spek, A. L. J. Organomet. Chem. 1998, 551, 67.
33. Ferrara, M. L. Giordano, F. Orabona, I. Panunzi, A. Ruffo, F. Eur. J. Inorg. Chem. 1999, 1939.
34. Fernandez-Galan, R. Jalon, F. A. Manzano, B. R. Rodriguez-de la Fuente, J. Vrahami, M. Jedlicka, B. Weissensteiner, W. Jogl, G. Organometallics 1997, 16, 3758.
35. Conard, C. R. Dolliver, M. A. Organic Syntheses; Wiley: New York, 1943; Collect. Vol. 2, p 167.
36. Rettig, M. F. Maitlis, P. M. Inorg. Synth. 1977, 17, 134.
37. (a) Bell, T. W. Guzzo, F. Drew, M. G. B. J. Am. Chem. Soc. 1991, 113, 3115.
38. (b) Crabb, T. A. Jackson, G. C. Org. Magn. Reson. 1975, 7, 488.
39. (c) Rülke, R. E. Delis, J. G. P. Groot, A. M. Elsevier, C. J. van Leeuwen, P. W. N. M. Vrieze, K. Goubitz, K. Schenk, H. J. Organomet. Chem. 1996, 508, 109.
40. (d) Mayer, K. H. Lauerer, D. Justus Liebigs Ann. Chem. 1970, 731, 142.
41. (e) Pointeau, P. Patin, H. Mousser, A. Le Marouille, J. Y. J. Organomet. Chem. 1986, 312, 263.
42. (f) Schnell, B. J. Heterocycl. Chem. 1999, 36, 541.
43. (g) Johnson, D. W. Mayer, H. K. Inorg. Chim. Acta 1987, 126, L1.
44. SAINT: SAX, Area Detector Integration; Siemens Analytical Instruments Inc., Madison, WI.
45. Sheldrick, G. SADABS: Siemens Area Detector Absorption Correction Software; University of Göttingen, Göttingen, Germany, 1996.
46. Altomare, A. Burla, M. C. Cavalli, M. Cascarano, G. Giacovazzo, C. Gagliardi, A. Moliterni, A. G. Polidori, G. Spagna, R. SIR97: A New Program For Solving And Refining Crystal Structures; Instituto di Ricerca per lo Sviluppo di Metodologie Cristallografiche CNR, Bari, Italy, 1997.
47. Sheldrick, G. SHELXL97: Program for Structure Refinement; University of Göttingen, Göttingen, Germany, 1997.
48. Farrugia, L. J. J. Appl. Crystallogr. 1999, 32, 837.
49. Allen, F. H. Kennard, O. Taylor, R. Acc. Chem. Res. 1983, 16, 146.