Probing the stereo-electronic properties of cationic rhodium complexes bearing chiral diphosphine ligands by 103Rh NMR

Magnetic Resonance in Chemistry

Volumn 48, Issue 11, 2010, Pages 848-856

  Fabrello, Amandine ^a,b   Dinoi, Chiara ^c,d   Perrin, Lionel ^c,d   Kalck, Philippe ^a,b   Maron, Laurent ^c,d   Urrutigoity, Martine ^a,b   Dechy Cabaret, Odile ^a,b  

^a LCC LABORATOIRE DE CHIMIE DE COORDINATION   (France)

^b UNIVERSITÉ DE TOULOUSE   (France)

^c INSA   (France)

^d CNRS   (France)

Author keywords

DFT; diphosphine; IR; rhodium complexes

Indexed keywords

CHEMICAL SHIFT; ELECTRONIC PROPERTIES; HYDROGENATION; IRIDIUM COMPOUNDS; LIGANDS; RHODIUM COMPOUNDS; STEREOCHEMISTRY;

CATIONICS; CO STRETCHING FREQUENCIES; DFT; DIPHOSPHINE LIGAND; DIPHOSPHINES; FREQUENCY MEASUREMENTS; IR; NMR MEASUREMENTS; RHODIUM COMPLEXES; STERICS;

SCAFFOLDS;

EID: 78649710963     PISSN: 07491581     EISSN: 1097458X     Source Type: Journal    
DOI: 10.1002/mrc.2677     Document Type: Article

References (57)

1. S. Gladiali, E. Alberico, in Phosphorus Ligands in Asymmetric Catalysis, (Eds:, A. Börner,), Wiley-VCH: Weinheim, 2008, pp 71.
2. J. G. de Vries, C. J. Elsevier, The Handbook of Homogeneous Hydrogenation, vol. 1-3, Wiley-VCH: Weinheim, 2007.
3. O. Kühl, Coord. Chem. Rev. 2005, 249, 693, DOI: 10.1016/ j.ccr.2004.08.021.
4. (a), C. A. Tolman, Chem. Rev. 1977, 77, 313, DOI: 10.1021/ cr60307a002
5. (b), T. Allman, R. G. Goel, Can. J. Chem. 1982, 60, 716.
6. D. R. Anton, R. H. Crabtree, Organometallics 1983, 2, 621, DOI: 10.1021/om00077a009.
7. S. Jeulin, S. Duprat de Paule, V. Ratovelomanana-Vidal, J.-P. Genêt, N. Champion, P. Dellis, PNAS 2004, 101, 5799, DOI: 10.1073/pnas.0307620101.
8. W. von Philipsborn, Chem. Soc. Rev. 1999, 28, 95.
9. P. A. Evans, Modern Rhodium-Catalyzed Organic Reactions, Wiley-VCH: Weinheim, 2007.
10. J. M. Ernsting, S. Gaemers, C. J. Elsevier, Magn. Reson. Chem. 2004, 42, 721, DOI: 10.1002/mrc.1439.
11. W. von Philipsborn, Pure Appl. Chem. 1986, 58, 513.
12. W. Leitner, M. Bühl, R. Fornika, C. Six, W. Baumann, E. Dinjus, M. Kessler, C. Krüger, A. Rufinska, Organometallics 1999, 18, 1196, DOI: 10.1021/om980980.
13. F. R. Bregman, J. M. Ernsting, F. Müller, M. D. K. Boele, L. A. van der Veen, C. J. Elsevier, J. Organomet. Chem. 1999, 592, 306, DOI: S0022-328X(99)00620-8.
14. C. J. Elsevier, B. Kowall, H. Kragten, Inorg. Chem. 1995, 34, 4836, DOI: 10.1021/ic00123a018.
15. L. Carlton, Magn. Reson. Chem. 2004, 42, 760, DOI: 10.1002/mrc.1437.
16. S. Filipuzzi, E. Männel, P. S. Pregosin, A. Albinati, S. Rizzato, L. F. Veiros, Organometallics 2008, 27, 4580, DOI: 10.1021/om800082c.
17. J. M. Ernsting, C. J. Elsevier, W. G. J. de Lange, K. Timmer, Magn. Reson. Chem. 1991, 29, S118, DOI: 10.1002/mrc.1260291320.
18. M. Bühl, W. Baumann, R. Kadyrov, A. Börner, Helv. Chim. Acta 1999, 82, 811, DOI: 10.1002/(SICI)1522-2675(19990609)82:6 < 811::AID-HLCA811 > 3.0.CO;2-O.
19. A. Börner, Eur. J. Inorg. Chem. 2001, 327-337,and references quoted therein, DOI: 10.1002/1099-0682(200102)2001:2<;327::AID-EJIC327 > 3.0.CO;2-A.
20. P. G. A. Kumar, P. S. Pregosin, T. M. Schmid, G. Consiglio, Magn. Reson. Chem. 2004, 42, 795, DOI: 10.1002/mrc.1406.
21. A. Fabrello, A. Bachelier, M. UrrutigoAty, P. Kalck, Coord. Chem. Rev. 2010, 254, 273, DOI:10.1016/j.ccr.2009.09.002.
22. (a), T. P. Dang, H. B. Kagan, J. Chem. Soc. D, Chem. Commun. 1971, 481. DOI: 10.1039/C29710000481
23. (b), T. P. Dang, H. B. Kagan, J. Am. Chem. Soc. 1972, 94, 6429, DOI: 10.1021/ja00773a028.
24. H. Shimizu, I. Nagasaki, T. Saito, Tetrahedron 2005, 61, 5405, DOI: 10.1016/j.tet.2005.03.022.
25. (a), M. J. Burk, Y. M. Wang, J. R. Lee, J. Am. Chem. Soc. 1996, 118, 5142, DOI: 10.1021/ja953872n
26. (b), M. J. Burk, Acc. Chem. Res. 2000, 33, 363, DOI: 10.1021/ar990085c.
27. (a), I. D. Gridnev, T. Imamoto, G. Hoge, M. Kouchi, H. Takahashi, J. Am. Chem. Soc. 2008, 130, 2560, DOI: 10.1021/ja076542z
28. (b), Y. Musashi, S. Sakaki, J. Am. Chem. Soc. 2002, 124, 7588, DOI: 10.1021/ja020063c
29. (c), M. A. Iron, A. Sundermann, J. M. L. Martin, J. Am. Chem. Soc. 2003, 125, 11430, DOI: 10.1021/ja028489e.
30. ORTEP3-, L. J. Farrugia, J. Appl. Crystallogr. 1997, 30, 565, DOI: 10.1107/C0021889897003117.
31. (a), H. Berger, R. Nesper, P. S. Pregosin, H. Ruegger, M. Wörle, Helv. Chim. Acta 1993, 76, 1520, DOI: 10.1002/hlca.19930760413
32. (b), N. Feiken, P. S. Pregosin, G. Trabesinger, Organometallics 1998, 17, 4510, DOI: 10.1021/om9802008
33. (c), H. Valentini, K. Selvakumar, M. Wörle, P. S. Pregosin, J. Organomet. Chem. 1999, 587, 244, DOI: 10.1016/S0022-328X(99)00329-0
34. (d), D. W. Price, M. G. B. Drew, K. K. Hii, J. M. Brown, Chem. Eur. J. 2000, 6, 4587, DOI: 10.1002/1521 3765(20001215)6:24<;4587::AID-CHEM4587 > 3.0.CO;2-6.
35. S. Dapprich, G. Frenking, J. Phys. Chem. 1995, 99, 9352, DOI: 10.1021/j100023a009.
36. C. J. den Reijer, M. Wörle, P. S. Pregosin, Organometallics 2000, 19, 309, DOI: 10.1021/om990714m.
37. (a), M. Aresta, E. Quaranta, A. Albinati, Organometallics 1993, 12, 2032, DOI: 10.1021/om00030a012
38. (b), F. Torres, E. Sola, M. Martín, C. Ochs, G. Picazo, J. A. López, F. J. Lahoz, L. A. Oro, Organometallics 2001, 20, 2716, DOI: 10.1021/om010024u.
39. E. Lindner, R. Fawzi, H. A. Mayer, K. Eichele, W. Hiller, Organometallics 1992, 11, 1033, DOI: 10.1021/om00039a007.
40. L. Perrin, E. Clot, O. Eisenstein, J. Loch, R. H. Crabtree, Inorg. Chem. 2001, 40, 5806, DOI: 10.1021/ic0105258.
41. D. Heller, H.-J. Drexler, J. You, W. Baumann, K. Drauz, H.-P. Krimmer, A. Börner, Chem. Eur. J. 2002, 8, 5196, DOI: 10.1002/1521-3765(20021115)8: 22<;5196::AID-CHEM5196 > 3.0.CO;2-P.
42. L. Ohrström, Comments Inorg. Chem. 1996, 18, 305, DOI: 10.1080/02603599608033866.
43. R. R. Schrock, J. A. Osborn, J. Am. Chem. Soc. 1971, 93, 2397, DOI: 10.1021/ja00739a006.
44. A. Bax, J. Magn. Reson. 1983, 52, 76.
45. R. K. Harris, E. D. Becker, S. M. Cabral de Menezes, R. Goodfellow, P. Granger, Pure Appl. Chem. 2001, 73, 1795, DOI: 10.1006/snmr.2002.0063.
46. L. Carlton, Annu. Rep. NMR Spectrosc. 2008, 63, 49.
47. A. Altomare, G. Cascarano, C. Giacovazzo, and, A. Guagliardi, J. Appl. Crystallogr. 1993, 26, 343, DOI: 10.1107/S0021889892010331.
48. SHELX [Includes SHELXS97, SHELXL97, CIFTAB]-, G. M. Sheldrick, Acta Crystallogr. A 2008, A64, 112, DOI: 10.1107/S0108767307043930.
49. L. J. Farrugia, J. Appl. Cryst. 1999, 32, 837, DOI: 10.1107/ S0021889899006020.
50. A. J. C. Wilson, International Tables for Crystallography, vol. C, Kluwer Academic Publishers: Dordrecht, 1995.
51. (a), J. P. Perdew, J. A. Chevary, S. H. Vosko, K. A. Jackson, M. R. Pederson, D. J. Singh, C. Fiolhais, Phys. Rev. B 1992, 46, 6671, DOI:10.1103/PhysRevB.46.6671
52. (b), A. D. Becke, J. Chem. Phys. 1993, 98, 5648, DOI:10.1063/1.464913.
53. (a), D. Andrae, U. Haeussermann, M. Dolg, H. Stoll, H. Preuss, Theor. Chim. Acta 1990, 77, 123, DOI: 10.1007/BF01114537
54. (b), J. M. L. Martin, A. Sundermann, J. Chem. Phys. 2001, 114, 3408, DOI: 10.1063/1.1337864
55. (c), A. Bergner, M. Dolg, W. Kuechle, H. Stoll, H. Preuss, Mol. Phys. 1993, 80, 1431.
56. A. W. Ehlers, M. Boehme, S. Dapprich, A. Gobbi, A. Hoellwarth, V. Jonas, K. F. Koehler, R. Stegmann, A. Veldkamp, G. Frenking, Chem. Phys. Lett. 1993, 208, 111, DOI: 10.1002/1521-3765(20001215)6:24<;4587::AID-CHEM4587 > 3.0.CO;2-6.
57. P. C. Harihara, J. A. Pople, Theor. Chim. Acta 1973, 28, 213, DOI: 10.1007/BF00533485.