Dimethylsulfoxide as a Ligand for RhI and IrI Complexes - Isolation, Structure, and Reactivity Towards X-H Bonds (X = H, OH, OCH3)

Chemistry - A European Journal

Volumn 9, Issue 21, 2003, Pages 5237-5249

  Dorta, Reto ^a   Rozenberg, Haim ^a   Shimon, Linda J W ^a   Milstein, David ^a  

^a WEIZMANN INSTITUTE OF SCIENCE   (Israel)

Author keywords

Iridium; O ligands; Oxidative addition; Rhodium; S ligands

Indexed keywords

ADDITION REACTIONS; CHEMICAL BONDS; COMPLEXATION; CRYSTALLOGRAPHY; POSITIVE IONS; RHODIUM; STRUCTURE (COMPOSITION); SYNTHESIS (CHEMICAL); THERMODYNAMICS;

NEUTRAL SYSTEMS;

SULFUR COMPOUNDS;

2,2' BIPYRIDINE DERIVATIVE; ALKENE DERIVATIVE; BRIDGED COMPOUND; CATION; DIMER; DIMETHYL SULFOXIDE; HYDROGEN; IRIDIUM COMPLEX; METHANOL; RHODIUM COMPLEX; WATER;

ADDITION REACTION; ARTICLE; CHEMICAL ANALYSIS; CHEMICAL BINDING; CHEMICAL BOND; COMPLEX FORMATION; CRYSTALLOGRAPHY; HYDROGEN BOND; MOLECULE; OXIDATION; PRECURSOR; SUBSTITUTION REACTION; THERMODYNAMICS;

EID: 0344065573     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/chem.200305144     Document Type: Article

References (69)

1. a) R. S. Dickson in Organometallic Chemistry of Rhodium and Iridium (Eds.: P. M. Maitlis, F. G. A. Stone, R. West), Academic Press, London, 1983;
2. b) J. P. Collman, L. S. Hegedus, J. R. Norton, R. G. Finke, Principles and Applications of Organotransition Metal Chemistry, University Science, Mill Valley, 1987.
3. M. Calligaris, O. Carugo, Coord. Chem. Rev. 1996, 153, 83.
4. 2 was characterized based only on its IR spectrum, see: a) B. R. James, R. H. Morris, Can. J. Chem. 1980, 58, 399.
5. I-DMSO complexes was suggested, see: b) B. R. James, R. H. Morris, P. Kvintovics, Can. J. Chem. 1986, 64, 897.
6. a) Y. M. Y. Haddad, H. B. Henbest, J. Trocha-Grimshaw, J. Chem. Soc. Perkin Trans. 1 1974, 592, and references therein;
7. b) Y. M. Y. Haddad, H. B. Henbest, J. Husbands, T. R. B. Mitchell, J. Trocha-Grimshaw, J. Chem. Soc. Perkin Trans. 1 1974, 596, and references therein;
8. c) H. B. Henbest, J. Trocha-Grimshaw, J. Chem. Soc. Perkin Trans. 1 1974, 607, and references therein;
9. d) B. R. James, R. H. Morris, J. Chem. Soc. Chem. Comnun. 1978, 929, and references therein.
10. G. W. Parshall, S. D. Ittel, Homogeneous Catalysis, 2nd ed., Wiley, New York, 1992.
11. a) D. J. Cole-Hamilton, G. Wilkinson, Nouv. J. Chim. 1977, 1, 141;
12. b) T. Yoshida, T. Matsuda, T. Okano, S. Otsuka, J. Am. Chem. Soc. 1979, 101, 2027;
13. c) J. Gotzig, R. Werner, H. Werner, J. Organomet. Chem. 1985, 290, 99;
14. d) R. S. Paonessa, A. L. Prignano, W. C. Trogler, Organometallics 1985, 4, 647;
15. e) D. Milstein, J. C. Calabrese, I. D. Williams, J. Am. Chem. Soc. 1986, 108, 6387;
16. f) M. B. Sponsler, B. H. Weiller, P. O. Stoutland, R. G. Bergman, J. Am. Chem. Soc. 1989, 111, 6841;
17. g) R. C. Stevens, R. Bau, D. Milstein, O. Blum, T. Koetzle, J. Chem. Soc. Dalton Trans. 1990, 1429;
18. h) H. Werner, A. Michenfelder, M. Schulz, Angew. Chem. 1991, 103, 555; Angew. Chem. Int. Ed. Engl. 1991, 30, 596;
19. h) H. Werner, A. Michenfelder, M. Schulz, Angew. Chem. 1991, 103, 555; Angew. Chem. Int. Ed. Engl. 1991, 30, 596;
20. i) F. T. Ladipo, M. Kooti, J. S. Merola, Inorg. Chem. 1993, 32, 1681;
21. j) M. J. Burn, M. G. Fickes, J. F. Hartwig, F. J. Hollander, R. G. Bergman, J. Am. Chem. Soc. 1993, 115, 5875;
22. k) O. Blum, D. Milstein, Angew. Chem. 1995, 107, 210; Angew. Chem. Int. Ed. Engl. 1995, 34, 229;
23. k) O. Blum, D. Milstein, Angew. Chem. 1995, 107, 210; Angew. Chem. Int. Ed. Engl. 1995, 34, 229;
24. l) R. Dorta, A. Togni, Organometallics 1998, 17, 3423;
25. m) K. Tani, A. Iseki, T. Yamagata, Angew. Chem. 1998, 110, 3590; Angew. Chem. Int. Ed. Engl. 1998, 37, 3381;
26. m) K. Tani, A. Iseki, T. Yamagata, Angew. Chem. 1998, 110, 3590; Angew. Chem. Int. Ed. Engl. 1998, 37, 3381;
27. n) D. Morales-Morales, D. W. Lee, Z. Wang, C. M. Jensen, Organometallics 2001, 20, 1144;
28. o) O. Blum, D. Milstein, J. Am. Chem. Soc. 2002, 124, 11456.
29. a) R. Dorta, H. Rozenberg, L. J. W. Shimon, D. Milstein, J. Am. Chem. Soc. 2002, 124, 188;
30. b) R. Dorta, H. Rozenberg, D. Milstein, Chem. Commun. 2002, 710.
31. 4] may actually be complex 1, see reference [3].
32. A. Cusanelli, U. Frey, A. E. Merbach, Chem. Commun. 1997, 379.
33. It has been shown for other transition-metal complexes that the trans arrangement of S-bound DMSO is not very favorable, see reference [2].
34. M. J. Bennett, P. B. Donaldson, Inorg. Chem. 1977, 16, 655.
35. 3] have never been characterized by X-ray crystallography, and thus structural comparison of complex 2 with its phosphine analogues was not possible.
36. T. Tamase, T. Aiko, Y. Yamamoto, Chem. Commun. 1996, 2341.
37. S. Geremia, S. Mestroni, M. Calligaris, E. Allesio, J. Chem. Soc. Dalton Trans. 1998, 2447.
38. F. A. Cotton, E. V. Dikarev, M. A. Petrukhina, S.-E. Stiriba, Inorg. Chem. 2000, 39, 1748; these two compounds were obtained by synthesis in the absence of solvent, and could only be observed in the solid state.
39. M. Calligaris, P. Faleschini, E. Alessio, Acta Crystallogr. Sect. C 1991, 47, 747.
40. E. Alessio, P. Faleschini, A. Sessanta o Santi, G. Mestroni, M. Calligaris, Inorg. Chem. 1993, 32, 5756.
41. 2] towards phosphine ligands, see: B. Denise, G. Pannetier, J. Organomet. Chem. 1978, 148, 155, and references therein.
42. These compounds are excellent hydrogenation catalysts, for example: W. De Aquino, R. Bonnaire, C. Potvin, J. Organomet. Chem. 1978, 154, 159, and references cited therein.
43. D. A. Ortmann, B. Weberndörfer, K. Ilg, M. Laubender, H. Werner, Organometallics 2002, 21, 2369.
44. For reactivity studies of complexes 9 and 13, see: R. Dorta, L. J. W. Shimon, H. Rozenberg, D. Milstein, Eur. J. Inorg. Chem. 2002, 1827.
45. Complex 10 reacts with benzyl chloride in much the same way as complex 9; R. Dorta, D. Milstein, unpublished results.
46. M. Green T. A. Kuc, J. Chem. Soc. Dalton Trans. 1972, 832.
47. B. R. James, R. H. Morris, K. J. Reimer, Can. J. Chem. 1977, 55, 2353.
48. For details see the data deposited at the CCDC.
49. I-COD complexes. Chelating ethylene-bridged bis(sulfoxides) of this kind have been characterized based on spectroscopic data, see: a) C. Pettinari M. Pellei, G. Cavicchio, M. Crucianelli, W. Panzeri, M. Colapietro, A. Cassetta, Organometallics 1999, 18, 555;
50. b) D. R. Evans, M. Huang, W. M. Seganish, J. C. Fettinger, T. L. Williams, Inorg. Chem. Commun. 2003, 6, 462.
51. 6, see: a) B. Windmuller, O. Nürnberg, J. Wolf, H. Werner, Eur. J. Inorg. Chem. 1999, 613;
52. for its X-ray structure, see: b) H. Werner, M. E. Schneider, M. Bosch, J. Wolf, J. H. Teuben, A. Meetsma, S. I. Troyanov, Chem. Eur. J. 2000, 6, 3052.
53. For the isolation, characterization, as well as the reactivity of this complex towards alkylphosphines, see: R. Dorta, R. Goikhman, D. Milstein, Organometallics 2003, 22, 2806.
54. H. M. Lee, T. Jiang, E. D. Stevens, S. P. Nolan, Organometallics 2001, 20, 1255.
55. M. S. Abbassioun, P. B. Hitchcock, P. A. Chaloner, Acta Crystallogr. Sect. C 1989, 45, 953.
56. 1H NMR signals at a significantly lower field than cis-dihydride ones, see for example: a) S. Nemeh, R. J. Flesher, K. Gierling, C. Maichle-Mossmer, H. A. Mayer, W. C. Kaska, Organometallics 1998, 17, 2003;
57. b) B. Rybtchinksi, Y. Ben-David, D. Milstein, Organometallics 1997, 16, 3786.
58. Analysis of the rate is approximate as the DMSO molecules of the starting complex exchange rapidly with the deuterated solvent. Thus, completion of the reaction was observed by comparing the integration of the hydride peak with the signal for one of the free, non-deuterated DMSO molecules.
59. For a review, see: B. R. James in Comprehensive Organometallic Chemistry (Eds.: G. Wilkinson, F. G. A. Stone, E. W. Abel), Pergamon, New York, 1982.
60. C. E. Johnson, R. Eisenberg, J. Am. Chem. Soc. 1985, 107, 3148.
61. 3] (R = methyl, ethyl) on the OH proton (see reference 6 o]). The fact that the 16-electron complexes 7 and 8 do not undergo water oxidative addition is probably a result of their not being nucleophilic enough on the one hand, and capable of forming a reactive 14-electron species on the other.
62. A. L. Casalnuovo, J. C. Calabrese, D. Milstein, J. Am. Chem. Soc. 1988, 110, 6738.
63. The NMR spectrum of a mixture of these two compounds did not give clear results because of the low solubility of these complexes and, possibly, because exchange processes rendered analysis difficult (see also the discussion of complexes 17 and 18).
64. 6 with water: R. Dorta, D. Milstein, unpublished results.
65. P. Hofmann, C. Meier, U. Englert, U. Schmidt, Chem. Ber. 1992, 125, 353.
66. R. H. Crabtree, S. M. Morehouse, J. M. Quirk, Inorg. Synth. 1986, 24, 173.
67. M. Green, T. A. Kuc, S. H. Taylor, J. Chem. Soc. A 1971, 2334.
68. A. Van der Ent, A. L. Onderlinden, Inorg. Synth. 1990, 28, 90.
69. G. M. Sheldrick, SHELX-97, Program for Crystal Structure Refinement, University of Göttingen, Göttingen (Germany), 1997