Facile and reversible O-H and C-H activation by a chiral iridium(I) complex

Organometallics

Volumn 17, Issue 16, 1998, Pages 3423-3428

  Dorta, Romano ^a   Togni, Antonio ^a  

^a ETH ZURICH   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001364548     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om980189b     Document Type: Article

References (45)

1. For the water gas shift reaction, see, e.g.: (a) Yoshida, T.; Ueda, Y.; Otsuka, S. J. Am. Chem. Soc. 1978, 100, 3941. (b) Yoshida, T.; Okano, T.; Ueda, Y.; Otsuka, S. J. Am. Chem. Soc. 1981, 103, 4311. For a recent report on Wacker-type chemistry, see: (c) Uozumi, Y.; Kato, K.; Hayashi, T. J. Am. Chem. Soc. 1997, 119, 5063. For nitrile and olefin hydration, see: (d) Bennett, M. A.; Yoshida, T. J. Am. Chem. Soc. 1973, 95, 3030. (e) Jensen, C. M.; Trogler, W. C. J. Am. Chem. Soc. 1986, 108, 723. For a preliminary report on transfer hydrogenation of alkynes, see: (f) Tani, K.; Iseki, A.; Yamagata, T. Abstract of Papers, 9th IUPAC Symposium on Organometallic Chemistry Directed Towards Organic Synthesis, Göttingen, Germany, 1997; Abstract 362.
2. For the water gas shift reaction, see, e.g.: (a) Yoshida, T.; Ueda, Y.; Otsuka, S. J. Am. Chem. Soc. 1978, 100, 3941. (b) Yoshida, T.; Okano, T.; Ueda, Y.; Otsuka, S. J. Am. Chem. Soc. 1981, 103, 4311. For a recent report on Wacker-type chemistry, see: (c) Uozumi, Y.; Kato, K.; Hayashi, T. J. Am. Chem. Soc. 1997, 119, 5063. For nitrile and olefin hydration, see: (d) Bennett, M. A.; Yoshida, T. J. Am. Chem. Soc. 1973, 95, 3030. (e) Jensen, C. M.; Trogler, W. C. J. Am. Chem. Soc. 1986, 108, 723. For a preliminary report on transfer hydrogenation of alkynes, see: (f) Tani, K.; Iseki, A.; Yamagata, T. Abstract of Papers, 9th IUPAC Symposium on Organometallic Chemistry Directed Towards Organic Synthesis, Göttingen, Germany, 1997; Abstract 362.
3. For the water gas shift reaction, see, e.g.: (a) Yoshida, T.; Ueda, Y.; Otsuka, S. J. Am. Chem. Soc. 1978, 100, 3941. (b) Yoshida, T.; Okano, T.; Ueda, Y.; Otsuka, S. J. Am. Chem. Soc. 1981, 103, 4311. For a recent report on Wacker-type chemistry, see: (c) Uozumi, Y.; Kato, K.; Hayashi, T. J. Am. Chem. Soc. 1997, 119, 5063. For nitrile and olefin hydration, see: (d) Bennett, M. A.; Yoshida, T. J. Am. Chem. Soc. 1973, 95, 3030. (e) Jensen, C. M.; Trogler, W. C. J. Am. Chem. Soc. 1986, 108, 723. For a preliminary report on transfer hydrogenation of alkynes, see: (f) Tani, K.; Iseki, A.; Yamagata, T. Abstract of Papers, 9th IUPAC Symposium on Organometallic Chemistry Directed Towards Organic Synthesis, Göttingen, Germany, 1997; Abstract 362.
4. For the water gas shift reaction, see, e.g.: (a) Yoshida, T.; Ueda, Y.; Otsuka, S. J. Am. Chem. Soc. 1978, 100, 3941. (b) Yoshida, T.; Okano, T.; Ueda, Y.; Otsuka, S. J. Am. Chem. Soc. 1981, 103, 4311. For a recent report on Wacker-type chemistry, see: (c) Uozumi, Y.; Kato, K.; Hayashi, T. J. Am. Chem. Soc. 1997, 119, 5063. For nitrile and olefin hydration, see: (d) Bennett, M. A.; Yoshida, T. J. Am. Chem. Soc. 1973, 95, 3030. (e) Jensen, C. M.; Trogler, W. C. J. Am. Chem. Soc. 1986, 108, 723. For a preliminary report on transfer hydrogenation of alkynes, see: (f) Tani, K.; Iseki, A.; Yamagata, T. Abstract of Papers, 9th IUPAC Symposium on Organometallic Chemistry Directed Towards Organic Synthesis, Göttingen, Germany, 1997; Abstract 362.
5. For the water gas shift reaction, see, e.g.: (a) Yoshida, T.; Ueda, Y.; Otsuka, S. J. Am. Chem. Soc. 1978, 100, 3941. (b) Yoshida, T.; Okano, T.; Ueda, Y.; Otsuka, S. J. Am. Chem. Soc. 1981, 103, 4311. For a recent report on Wacker-type chemistry, see: (c) Uozumi, Y.; Kato, K.; Hayashi, T. J. Am. Chem. Soc. 1997, 119, 5063. For nitrile and olefin hydration, see: (d) Bennett, M. A.; Yoshida, T. J. Am. Chem. Soc. 1973, 95, 3030. (e) Jensen, C. M.; Trogler, W. C. J. Am. Chem. Soc. 1986, 108, 723. For a preliminary report on transfer hydrogenation of alkynes, see: (f) Tani, K.; Iseki, A.; Yamagata, T. Abstract of Papers, 9th IUPAC Symposium on Organometallic Chemistry Directed Towards Organic Synthesis, Göttingen, Germany, 1997; Abstract 362.
6. For the water gas shift reaction, see, e.g.: (a) Yoshida, T.; Ueda, Y.; Otsuka, S. J. Am. Chem. Soc. 1978, 100, 3941. (b) Yoshida, T.; Okano, T.; Ueda, Y.; Otsuka, S. J. Am. Chem. Soc. 1981, 103, 4311. For a recent report on Wacker-type chemistry, see: (c) Uozumi, Y.; Kato, K.; Hayashi, T. J. Am. Chem. Soc. 1997, 119, 5063. For nitrile and olefin hydration, see: (d) Bennett, M. A.; Yoshida, T. J. Am. Chem. Soc. 1973, 95, 3030. (e) Jensen, C. M.; Trogler, W. C. J. Am. Chem. Soc. 1986, 108, 723. For a preliminary report on transfer hydrogenation of alkynes, see: (f) Tani, K.; Iseki, A.; Yamagata, T. Abstract of Papers, 9th IUPAC Symposium on Organometallic Chemistry Directed Towards Organic Synthesis, Göttingen, Germany, 1997; Abstract 362.
7. (a) Milstein, D.; Calabrese, J. C.; Williams, I. D. J. Am. Chem. Soc. 1986, 108, 6387.
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12. 3, see: (f) Koelliker, R.; Milstein, D. Angew. Chem. 1991, 103, 724.
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17. As opposed to oxidative addition, usually to electron-rich late-transition-metal species, the reaction of water with early-transition-metal or lanthanide complexes proceeds more typically in a hydrolytic manner or with loss of molecular hydrogen, as the result of a water reduction process. See, e.g.: (a) Guggenberger, L. J.; Tebbe, F. N. J. Am. Chem. Soc. 1976, 98, 4137. (b) Hillhouse, G. L.; Bercaw, J. E. J. Am. Chem. Soc. 1984, 106, 5472.
18. As opposed to oxidative addition, usually to electron-rich late-transition-metal species, the reaction of water with early-transition-metal or lanthanide complexes proceeds more typically in a hydrolytic manner or with loss of molecular hydrogen, as the result of a water reduction process. See, e.g.: (a) Guggenberger, L. J.; Tebbe, F. N. J. Am. Chem. Soc. 1976, 98, 4137. (b) Hillhouse, G. L.; Bercaw, J. E. J. Am. Chem. Soc. 1984, 106, 5472.
19. Arndtsen, B. A.; Bergman, R. G.; Mobley, T. A.; Peterson, T. H. Acc. Chem. Res. 1995, 28, 154. For a general review on C-H activation by metal complexes, see: Shilov, A. E.; Shul'pin, G. B. Chem. Rev. 1997, 97, 2879.
20. Arndtsen, B. A.; Bergman, R. G.; Mobley, T. A.; Peterson, T. H. Acc. Chem. Res. 1995, 28, 154. For a general review on C-H activation by metal complexes, see: Shilov, A. E.; Shul'pin, G. B. Chem. Rev. 1997, 97, 2879.
21. For examples, see: (a) Liou, S.-Y.; Gozin, M.; Milstein, D. J. Am. Chem. Soc. 1995, 117, 9774. (b) Hackett, M.; Ibers, J. A.; Jernakoff, P.; Whitesides, G. M. J. Am. Chem. Soc. 1986, 108, 8094. (c) Bulls, A. R.; Schaefer W. P.; Serfas, M.; Bercaw, J. E. Organometallics 1987, 6, 1219. (d) Buchanan, J. M.; Stryker, J. M.; Bergman, R. G. J. Am. Chem. Soc. 1986, 108, 1537.
22. For examples, see: (a) Liou, S.-Y.; Gozin, M.; Milstein, D. J. Am. Chem. Soc. 1995, 117, 9774. (b) Hackett, M.; Ibers, J. A.; Jernakoff, P.; Whitesides, G. M. J. Am. Chem. Soc. 1986, 108, 8094. (c) Bulls, A. R.; Schaefer W. P.; Serfas, M.; Bercaw, J. E. Organometallics 1987, 6, 1219. (d) Buchanan, J. M.; Stryker, J. M.; Bergman, R. G. J. Am. Chem. Soc. 1986, 108, 1537.
23. For examples, see: (a) Liou, S.-Y.; Gozin, M.; Milstein, D. J. Am. Chem. Soc. 1995, 117, 9774. (b) Hackett, M.; Ibers, J. A.; Jernakoff, P.; Whitesides, G. M. J. Am. Chem. Soc. 1986, 108, 8094. (c) Bulls, A. R.; Schaefer W. P.; Serfas, M.; Bercaw, J. E. Organometallics 1987, 6, 1219. (d) Buchanan, J. M.; Stryker, J. M.; Bergman, R. G. J. Am. Chem. Soc. 1986, 108, 1537.
24. For examples, see: (a) Liou, S.-Y.; Gozin, M.; Milstein, D. J. Am. Chem. Soc. 1995, 117, 9774. (b) Hackett, M.; Ibers, J. A.; Jernakoff, P.; Whitesides, G. M. J. Am. Chem. Soc. 1986, 108, 8094. (c) Bulls, A. R.; Schaefer W. P.; Serfas, M.; Bercaw, J. E. Organometallics 1987, 6, 1219. (d) Buchanan, J. M.; Stryker, J. M.; Bergman, R. G. J. Am. Chem. Soc. 1986, 108, 1537.
25. (a) Dorta, R.; Eglí, P.; Zürcher, F.; Togni, A. J. Am. Chem. Soc. 1997, 119, 10857.
26. The synthesis and characterization of complexes of type 1 was also reported by Tani and co-workers. See: (b) Yamagata, T.; Iseki, A.; Tani, K. Chem. Lett. 1997, 1215. For a derivative bearing a fluorinated trialkylphosphine, see: (c) Schnabel, R. C.; Roddick, D. M. Inorg. Chem. 1993, 32, 1513.
27. The synthesis and characterization of complexes of type 1 was also reported by Tani and co-workers. See: (b) Yamagata, T.; Iseki, A.; Tani, K. Chem. Lett. 1997, 1215. For a derivative bearing a fluorinated trialkylphosphine, see: (c) Schnabel, R. C.; Roddick, D. M. Inorg. Chem. 1993, 32, 1513.
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29. Dorta, R.; Togni, A. Unpublished results.
30. Driver and Hartwig have lately shown that a bridged Pd-hydroxo complex is more basic than the corresponding amido species in organic solvents. This stands in marked contrast with the relative basicities of alkali-metal hydroxides and amides, respectively. Thus, by analogy, catalyst formation might occur via amine deprotonation by syn-trans-3 and not via reductive elimination of water. See: (a) Driver, M. S.; Hartwig, J. F. Organometallics 1997, 16, 5706. (b) Driver, M. S.; Hartwig, J. F. J. Am. Chem. Soc. 1996, 118, 4206. (c) Hartwig, J. F. Synlett 1997, 329.
31. Driver and Hartwig have lately shown that a bridged Pd-hydroxo complex is more basic than the corresponding amido species in organic solvents. This stands in marked contrast with the relative basicities of alkali-metal hydroxides and amides, respectively. Thus, by analogy, catalyst formation might occur via amine deprotonation by syn-trans-3 and not via reductive elimination of water. See: (a) Driver, M. S.; Hartwig, J. F. Organometallics 1997, 16, 5706. (b) Driver, M. S.; Hartwig, J. F. J. Am. Chem. Soc. 1996, 118, 4206. (c) Hartwig, J. F. Synlett 1997, 329.
32. Driver and Hartwig have lately shown that a bridged Pd-hydroxo complex is more basic than the corresponding amido species in organic solvents. This stands in marked contrast with the relative basicities of alkali-metal hydroxides and amides, respectively. Thus, by analogy, catalyst formation might occur via amine deprotonation by syn-trans-3 and not via reductive elimination of water. See: (a) Driver, M. S.; Hartwig, J. F. Organometallics 1997, 16, 5706. (b) Driver, M. S.; Hartwig, J. F. J. Am. Chem. Soc. 1996, 118, 4206. (c) Hartwig, J. F. Synlett 1997, 329.
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35. For examples, see: (a) Nolte, M. J.; Van der Stock E.; Singleton, E. Inorg. Chim. Acta 1976, 19, L51. (b) Nolte, M. J., Singleton, E.; Van der Stock, E. Acta Crystallogr., Sect. B 1978, 34, 1684. (c) Roberts, P. J.; Ferguson, G. Acta Crystallogr., Sect. B 1976, 32, 1513. (d) Mueting, A. M.; Boyle, P. D.; Wagner, R.; Pignolet, L. H. Inorg. Chem. 1988, 27, 271. (e) Crabtree, R. H.; Felkin, H.; Morris, G. E.; King, T. J.; Richards, J. A. J. Organomet. Chem. 1976, 113, C7.
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41. For a discussion of structural aspects of Josiphos-type ligands, see: (a) Togni, A. In Organic Synthesis via Organometallics (OSM5); Helmchen, G., Dibo, J., Flubacher, D., Wiese, B., Eds.; Vieweg: Braunschweig, 1997; pp 185-208. (b) Togni, A.; Spindler, F.; Rihs, G.; Zanetti, N.; Soares, M. C.; Gerfin, T.; Gramlich, V. Inorg. Chim. Acta 1994, 222, 213.
42. For a discussion of structural aspects of Josiphos-type ligands, see: (a) Togni, A. In Organic Synthesis via Organometallics (OSM5); Helmchen, G., Dibo, J., Flubacher, D., Wiese, B., Eds.; Vieweg: Braunschweig, 1997; pp 185-208. (b) Togni, A.; Spindler, F.; Rihs, G.; Zanetti, N.; Soares, M. C.; Gerfin, T.; Gramlich, V. Inorg. Chim. Acta 1994, 222, 213.
43. 3 C-H activation, see: Farnetti, E.; Nardin, G.; Graziani, M. J. Chem. Soc., Chem. Commun. 1988, 1264.
44. For a recent example of a mononuclear hydrido-hydroxo complex, see: Kaplan, A. W.; Bergman, R. G. Organometallics 1997, 16, 1106 and references therein.
45. 2O.