Solvent-controlled selectivity toward exclusive C-C or C-H bond activation by a cationic metal center

Journal of the American Chemical Society

Volumn 121, Issue 18, 1999, Pages 4528-4529

  Rybtchinski, Boris ^a   Milstein, David ^a  

^a WEIZMANN INSTITUTE OF SCIENCE   (Israel)

Author keywords

[No Author keywords available]

Indexed keywords

CARBON; HYDROGEN; SOLVENT;

ARTICLE; CHEMICAL STRUCTURE; HYDROGEN BOND; MOLECULAR INTERACTION; MOLECULAR STABILITY; NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; THERMODYNAMICS;

EID: 0033549083     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja990339p     Document Type: Article

References (28)

1. For a review on C-C activation, see: Rybtchinski, B.; Milstein, D. Angew. Chem., Int. Ed. 1999, 38, 870.
2. For reviews on hydrocarbon activation, see: (a) Crabtree, R. H. Chem. Rev. 1985, 85, 245. (b) Arndtsen, B. A.; Bergman, R. G.; Mobley, T. A.; Peterson, T. H. Acc. Chem. Res. 1995, 28, 154. (c) Shilov, A. E.; Shul'pin, G. B. Chem. Rev. 1997 97, 2879 (d) Stahl, S. S.; Labinger, J. A.; Bercaw, J. E. Angew. Chem., Int. Ed. 1998, 37, 2180.
3. For reviews on hydrocarbon activation, see: (a) Crabtree, R. H. Chem. Rev. 1985, 85, 245. (b) Arndtsen, B. A.; Bergman, R. G.; Mobley, T. A.; Peterson, T. H. Acc. Chem. Res. 1995, 28, 154. (c) Shilov, A. E.; Shul'pin, G. B. Chem. Rev. 1997 97, 2879 (d) Stahl, S. S.; Labinger, J. A.; Bercaw, J. E. Angew. Chem., Int. Ed. 1998, 37, 2180.
4. For reviews on hydrocarbon activation, see: (a) Crabtree, R. H. Chem. Rev. 1985, 85, 245. (b) Arndtsen, B. A.; Bergman, R. G.; Mobley, T. A.; Peterson, T. H. Acc. Chem. Res. 1995, 28, 154. (c) Shilov, A. E.; Shul'pin, G. B. Chem. Rev. 1997 97, 2879 (d) Stahl, S. S.; Labinger, J. A.; Bercaw, J. E. Angew. Chem., Int. Ed. 1998, 37, 2180.
5. For reviews on hydrocarbon activation, see: (a) Crabtree, R. H. Chem. Rev. 1985, 85, 245. (b) Arndtsen, B. A.; Bergman, R. G.; Mobley, T. A.; Peterson, T. H. Acc. Chem. Res. 1995, 28, 154. (c) Shilov, A. E.; Shul'pin, G. B. Chem. Rev. 1997 97, 2879 (d) Stahl, S. S.; Labinger, J. A.; Bercaw, J. E. Angew. Chem., Int. Ed. 1998, 37, 2180.
6. For some examples of C-C bond activation in solution, see: (a) Cassar, L.; Eaton, P. E.; Halpern, J. J. Am. Chem. Soc. 1970, 92, 3515. (b) Periana, R. A.; Bergman, R. G. J. Am. Chem. Soc. 1986, 108, 7346. (c) Perthuisot, C.; Jones, W. D. J. Am. Chem. Soc. 1994, 116, 3647. (d) Suggs, J. W.; Jun, C.- H. J. Am. Chem. Soc. 1984, 106, 3054. (e) Murakami, M.; Amii, H.; Ito, Y. Nature 1994, 370, 540. (f) Crabtree, R. H.; Dion, R. P.; Gibboni, D. J.; McGrath, D. V.; Holt, E. M. J. Am. Chem. Soc. 1986, 108, 7222. (g) Bennett, M. A.; Nicholls, J. C.; Rahman, A. K. F.; Redhouse, A. D.; Spencer, J. L.; Willis A. C. J. Chem. Soc., Chem. Commun. 1989, 1328. (h) Suzuki, H.; Takaya, Y.; Takemori, T. J. Am. Chem. Soc. 1994, 116, 10779. (i) Pulst, S.; Kirchbauer, F. G.; Heller, B.; Baumann, W.; Rosenthal U. Angew. Chem., Int. Ed. 1998, 37, 1925.
7. For some examples of C-C bond activation in solution, see: (a) Cassar, L.; Eaton, P. E.; Halpern, J. J. Am. Chem. Soc. 1970, 92, 3515. (b) Periana, R. A.; Bergman, R. G. J. Am. Chem. Soc. 1986, 108, 7346. (c) Perthuisot, C.; Jones, W. D. J. Am. Chem. Soc. 1994, 116, 3647. (d) Suggs, J. W.; Jun, C.- H. J. Am. Chem. Soc. 1984, 106, 3054. (e) Murakami, M.; Amii, H.; Ito, Y. Nature 1994, 370, 540. (f) Crabtree, R. H.; Dion, R. P.; Gibboni, D. J.; McGrath, D. V.; Holt, E. M. J. Am. Chem. Soc. 1986, 108, 7222. (g) Bennett, M. A.; Nicholls, J. C.; Rahman, A. K. F.; Redhouse, A. D.; Spencer, J. L.; Willis A. C. J. Chem. Soc., Chem. Commun. 1989, 1328. (h) Suzuki, H.; Takaya, Y.; Takemori, T. J. Am. Chem. Soc. 1994, 116, 10779. (i) Pulst, S.; Kirchbauer, F. G.; Heller, B.; Baumann, W.; Rosenthal U. Angew. Chem., Int. Ed. 1998, 37, 1925.
8. For some examples of C-C bond activation in solution, see: (a) Cassar, L.; Eaton, P. E.; Halpern, J. J. Am. Chem. Soc. 1970, 92, 3515. (b) Periana, R. A.; Bergman, R. G. J. Am. Chem. Soc. 1986, 108, 7346. (c) Perthuisot, C.; Jones, W. D. J. Am. Chem. Soc. 1994, 116, 3647. (d) Suggs, J. W.; Jun, C.- H. J. Am. Chem. Soc. 1984, 106, 3054. (e) Murakami, M.; Amii, H.; Ito, Y. Nature 1994, 370, 540. (f) Crabtree, R. H.; Dion, R. P.; Gibboni, D. J.; McGrath, D. V.; Holt, E. M. J. Am. Chem. Soc. 1986, 108, 7222. (g) Bennett, M. A.; Nicholls, J. C.; Rahman, A. K. F.; Redhouse, A. D.; Spencer, J. L.; Willis A. C. J. Chem. Soc., Chem. Commun. 1989, 1328. (h) Suzuki, H.; Takaya, Y.; Takemori, T. J. Am. Chem. Soc. 1994, 116, 10779. (i) Pulst, S.; Kirchbauer, F. G.; Heller, B.; Baumann, W.; Rosenthal U. Angew. Chem., Int. Ed. 1998, 37, 1925.
9. For some examples of C-C bond activation in solution, see: (a) Cassar, L.; Eaton, P. E.; Halpern, J. J. Am. Chem. Soc. 1970, 92, 3515. (b) Periana, R. A.; Bergman, R. G. J. Am. Chem. Soc. 1986, 108, 7346. (c) Perthuisot, C.; Jones, W. D. J. Am. Chem. Soc. 1994, 116, 3647. (d) Suggs, J. W.; Jun, C.- H. J. Am. Chem. Soc. 1984, 106, 3054. (e) Murakami, M.; Amii, H.; Ito, Y. Nature 1994, 370, 540. (f) Crabtree, R. H.; Dion, R. P.; Gibboni, D. J.; McGrath, D. V.; Holt, E. M. J. Am. Chem. Soc. 1986, 108, 7222. (g) Bennett, M. A.; Nicholls, J. C.; Rahman, A. K. F.; Redhouse, A. D.; Spencer, J. L.; Willis A. C. J. Chem. Soc., Chem. Commun. 1989, 1328. (h) Suzuki, H.; Takaya, Y.; Takemori, T. J. Am. Chem. Soc. 1994, 116, 10779. (i) Pulst, S.; Kirchbauer, F. G.; Heller, B.; Baumann, W.; Rosenthal U. Angew. Chem., Int. Ed. 1998, 37, 1925.
10. For some examples of C-C bond activation in solution, see: (a) Cassar, L.; Eaton, P. E.; Halpern, J. J. Am. Chem. Soc. 1970, 92, 3515. (b) Periana, R. A.; Bergman, R. G. J. Am. Chem. Soc. 1986, 108, 7346. (c) Perthuisot, C.; Jones, W. D. J. Am. Chem. Soc. 1994, 116, 3647. (d) Suggs, J. W.; Jun, C.- H. J. Am. Chem. Soc. 1984, 106, 3054. (e) Murakami, M.; Amii, H.; Ito, Y. Nature 1994, 370, 540. (f) Crabtree, R. H.; Dion, R. P.; Gibboni, D. J.; McGrath, D. V.; Holt, E. M. J. Am. Chem. Soc. 1986, 108, 7222. (g) Bennett, M. A.; Nicholls, J. C.; Rahman, A. K. F.; Redhouse, A. D.; Spencer, J. L.; Willis A. C. J. Chem. Soc., Chem. Commun. 1989, 1328. (h) Suzuki, H.; Takaya, Y.; Takemori, T. J. Am. Chem. Soc. 1994, 116, 10779. (i) Pulst, S.; Kirchbauer, F. G.; Heller, B.; Baumann, W.; Rosenthal U. Angew. Chem., Int. Ed. 1998, 37, 1925.
11. For some examples of C-C bond activation in solution, see: (a) Cassar, L.; Eaton, P. E.; Halpern, J. J. Am. Chem. Soc. 1970, 92, 3515. (b) Periana, R. A.; Bergman, R. G. J. Am. Chem. Soc. 1986, 108, 7346. (c) Perthuisot, C.; Jones, W. D. J. Am. Chem. Soc. 1994, 116, 3647. (d) Suggs, J. W.; Jun, C.- H. J. Am. Chem. Soc. 1984, 106, 3054. (e) Murakami, M.; Amii, H.; Ito, Y. Nature 1994, 370, 540. (f) Crabtree, R. H.; Dion, R. P.; Gibboni, D. J.; McGrath, D. V.; Holt, E. M. J. Am. Chem. Soc. 1986, 108, 7222. (g) Bennett, M. A.; Nicholls, J. C.; Rahman, A. K. F.; Redhouse, A. D.; Spencer, J. L.; Willis A. C. J. Chem. Soc., Chem. Commun. 1989, 1328. (h) Suzuki, H.; Takaya, Y.; Takemori, T. J. Am. Chem. Soc. 1994, 116, 10779. (i) Pulst, S.; Kirchbauer, F. G.; Heller, B.; Baumann, W.; Rosenthal U. Angew. Chem., Int. Ed. 1998, 37, 1925.
12. For some examples of C-C bond activation in solution, see: (a) Cassar, L.; Eaton, P. E.; Halpern, J. J. Am. Chem. Soc. 1970, 92, 3515. (b) Periana, R. A.; Bergman, R. G. J. Am. Chem. Soc. 1986, 108, 7346. (c) Perthuisot, C.; Jones, W. D. J. Am. Chem. Soc. 1994, 116, 3647. (d) Suggs, J. W.; Jun, C.- H. J. Am. Chem. Soc. 1984, 106, 3054. (e) Murakami, M.; Amii, H.; Ito, Y. Nature 1994, 370, 540. (f) Crabtree, R. H.; Dion, R. P.; Gibboni, D. J.; McGrath, D. V.; Holt, E. M. J. Am. Chem. Soc. 1986, 108, 7222. (g) Bennett, M. A.; Nicholls, J. C.; Rahman, A. K. F.; Redhouse, A. D.; Spencer, J. L.; Willis A. C. J. Chem. Soc., Chem. Commun. 1989, 1328. (h) Suzuki, H.; Takaya, Y.; Takemori, T. J. Am. Chem. Soc. 1994, 116, 10779. (i) Pulst, S.; Kirchbauer, F. G.; Heller, B.; Baumann, W.; Rosenthal U. Angew. Chem., Int. Ed. 1998, 37, 1925.
13. For some examples of C-C bond activation in solution, see: (a) Cassar, L.; Eaton, P. E.; Halpern, J. J. Am. Chem. Soc. 1970, 92, 3515. (b) Periana, R. A.; Bergman, R. G. J. Am. Chem. Soc. 1986, 108, 7346. (c) Perthuisot, C.; Jones, W. D. J. Am. Chem. Soc. 1994, 116, 3647. (d) Suggs, J. W.; Jun, C.- H. J. Am. Chem. Soc. 1984, 106, 3054. (e) Murakami, M.; Amii, H.; Ito, Y. Nature 1994, 370, 540. (f) Crabtree, R. H.; Dion, R. P.; Gibboni, D. J.; McGrath, D. V.; Holt, E. M. J. Am. Chem. Soc. 1986, 108, 7222. (g) Bennett, M. A.; Nicholls, J. C.; Rahman, A. K. F.; Redhouse, A. D.; Spencer, J. L.; Willis A. C. J. Chem. Soc., Chem. Commun. 1989, 1328. (h) Suzuki, H.; Takaya, Y.; Takemori, T. J. Am. Chem. Soc. 1994, 116, 10779. (i) Pulst, S.; Kirchbauer, F. G.; Heller, B.; Baumann, W.; Rosenthal U. Angew. Chem., Int. Ed. 1998, 37, 1925.
14. For some examples of C-C bond activation in solution, see: (a) Cassar, L.; Eaton, P. E.; Halpern, J. J. Am. Chem. Soc. 1970, 92, 3515. (b) Periana, R. A.; Bergman, R. G. J. Am. Chem. Soc. 1986, 108, 7346. (c) Perthuisot, C.; Jones, W. D. J. Am. Chem. Soc. 1994, 116, 3647. (d) Suggs, J. W.; Jun, C.- H. J. Am. Chem. Soc. 1984, 106, 3054. (e) Murakami, M.; Amii, H.; Ito, Y. Nature 1994, 370, 540. (f) Crabtree, R. H.; Dion, R. P.; Gibboni, D. J.; McGrath, D. V.; Holt, E. M. J. Am. Chem. Soc. 1986, 108, 7222. (g) Bennett, M. A.; Nicholls, J. C.; Rahman, A. K. F.; Redhouse, A. D.; Spencer, J. L.; Willis A. C. J. Chem. Soc., Chem. Commun. 1989, 1328. (h) Suzuki, H.; Takaya, Y.; Takemori, T. J. Am. Chem. Soc. 1994, 116, 10779. (i) Pulst, S.; Kirchbauer, F. G.; Heller, B.; Baumann, W.; Rosenthal U. Angew. Chem., Int. Ed. 1998, 37, 1925.
15. For some examples of C-C bond activation in PCP systems, see: (a) Gozin, M.; Weisman, A.; Ben-David, Y.; Milstein, D. Nature 1993, 364, 699. (b) Liou, Sh.-Y.; Gozin, M.; Milstein, D. J. Am. Chem. Soc. 1995, 117, 9774. (c) Liou, Sh.-Y.; Gozin, M.; Milstein, D. J. Chem. Soc., Chem. Commun. 1995, 1965. (d) Rybtchinski, B.; Vigalok, A.; Ben-David, Y.; Milstein, D. J. Am. Chem. Soc. 1996, 118, 12406. (e) van der Boom, M. E.; Kraatz, H.-B.; Ben-David, Y.; Milstein, D. Chem. Commun. 1996, 2167. (f) Liou, Sh.-Y.; van der Boom, M. E.; Milstein, D. Chem. Commun. 1998, 687. (g) van der Boom, M. E.; Liou, Sh.-Y.; Ben-David, Y.; Gozin, M.; Milstein, D. J. Am. Chem. Soc. 1998, 120, 13415.
16. For some examples of C-C bond activation in PCP systems, see: (a) Gozin, M.; Weisman, A.; Ben-David, Y.; Milstein, D. Nature 1993, 364, 699. (b) Liou, Sh.-Y.; Gozin, M.; Milstein, D. J. Am. Chem. Soc. 1995, 117, 9774. (c) Liou, Sh.-Y.; Gozin, M.; Milstein, D. J. Chem. Soc., Chem. Commun. 1995, 1965. (d) Rybtchinski, B.; Vigalok, A.; Ben-David, Y.; Milstein, D. J. Am. Chem. Soc. 1996, 118, 12406. (e) van der Boom, M. E.; Kraatz, H.-B.; Ben-David, Y.; Milstein, D. Chem. Commun. 1996, 2167. (f) Liou, Sh.-Y.; van der Boom, M. E.; Milstein, D. Chem. Commun. 1998, 687. (g) van der Boom, M. E.; Liou, Sh.-Y.; Ben-David, Y.; Gozin, M.; Milstein, D. J. Am. Chem. Soc. 1998, 120, 13415.
17. For some examples of C-C bond activation in PCP systems, see: (a) Gozin, M.; Weisman, A.; Ben-David, Y.; Milstein, D. Nature 1993, 364, 699. (b) Liou, Sh.-Y.; Gozin, M.; Milstein, D. J. Am. Chem. Soc. 1995, 117, 9774. (c) Liou, Sh.-Y.; Gozin, M.; Milstein, D. J. Chem. Soc., Chem. Commun. 1995, 1965. (d) Rybtchinski, B.; Vigalok, A.; Ben-David, Y.; Milstein, D. J. Am. Chem. Soc. 1996, 118, 12406. (e) van der Boom, M. E.; Kraatz, H.-B.; Ben-David, Y.; Milstein, D. Chem. Commun. 1996, 2167. (f) Liou, Sh.-Y.; van der Boom, M. E.; Milstein, D. Chem. Commun. 1998, 687. (g) van der Boom, M. E.; Liou, Sh.-Y.; Ben-David, Y.; Gozin, M.; Milstein, D. J. Am. Chem. Soc. 1998, 120, 13415.
18. For some examples of C-C bond activation in PCP systems, see: (a) Gozin, M.; Weisman, A.; Ben-David, Y.; Milstein, D. Nature 1993, 364, 699. (b) Liou, Sh.-Y.; Gozin, M.; Milstein, D. J. Am. Chem. Soc. 1995, 117, 9774. (c) Liou, Sh.-Y.; Gozin, M.; Milstein, D. J. Chem. Soc., Chem. Commun. 1995, 1965. (d) Rybtchinski, B.; Vigalok, A.; Ben-David, Y.; Milstein, D. J. Am. Chem. Soc. 1996, 118, 12406. (e) van der Boom, M. E.; Kraatz, H.-B.; Ben-David, Y.; Milstein, D. Chem. Commun. 1996, 2167. (f) Liou, Sh.-Y.; van der Boom, M. E.; Milstein, D. Chem. Commun. 1998, 687. (g) van der Boom, M. E.; Liou, Sh.-Y.; Ben-David, Y.; Gozin, M.; Milstein, D. J. Am. Chem. Soc. 1998, 120, 13415.
19. For some examples of C-C bond activation in PCP systems, see: (a) Gozin, M.; Weisman, A.; Ben-David, Y.; Milstein, D. Nature 1993, 364, 699. (b) Liou, Sh.-Y.; Gozin, M.; Milstein, D. J. Am. Chem. Soc. 1995, 117, 9774. (c) Liou, Sh.-Y.; Gozin, M.; Milstein, D. J. Chem. Soc., Chem. Commun. 1995, 1965. (d) Rybtchinski, B.; Vigalok, A.; Ben-David, Y.; Milstein, D. J. Am. Chem. Soc. 1996, 118, 12406. (e) van der Boom, M. E.; Kraatz, H.-B.; Ben-David, Y.; Milstein, D. Chem. Commun. 1996, 2167. (f) Liou, Sh.-Y.; van der Boom, M. E.; Milstein, D. Chem. Commun. 1998, 687. (g) van der Boom, M. E.; Liou, Sh.-Y.; Ben-David, Y.; Gozin, M.; Milstein, D. J. Am. Chem. Soc. 1998, 120, 13415.
20. For some examples of C-C bond activation in PCP systems, see: (a) Gozin, M.; Weisman, A.; Ben-David, Y.; Milstein, D. Nature 1993, 364, 699. (b) Liou, Sh.-Y.; Gozin, M.; Milstein, D. J. Am. Chem. Soc. 1995, 117, 9774. (c) Liou, Sh.-Y.; Gozin, M.; Milstein, D. J. Chem. Soc., Chem. Commun. 1995, 1965. (d) Rybtchinski, B.; Vigalok, A.; Ben-David, Y.; Milstein, D. J. Am. Chem. Soc. 1996, 118, 12406. (e) van der Boom, M. E.; Kraatz, H.-B.; Ben-David, Y.; Milstein, D. Chem. Commun. 1996, 2167. (f) Liou, Sh.-Y.; van der Boom, M. E.; Milstein, D. Chem. Commun. 1998, 687. (g) van der Boom, M. E.; Liou, Sh.-Y.; Ben-David, Y.; Gozin, M.; Milstein, D. J. Am. Chem. Soc. 1998, 120, 13415.
21. For some examples of C-C bond activation in PCP systems, see: (a) Gozin, M.; Weisman, A.; Ben-David, Y.; Milstein, D. Nature 1993, 364, 699. (b) Liou, Sh.-Y.; Gozin, M.; Milstein, D. J. Am. Chem. Soc. 1995, 117, 9774. (c) Liou, Sh.-Y.; Gozin, M.; Milstein, D. J. Chem. Soc., Chem. Commun. 1995, 1965. (d) Rybtchinski, B.; Vigalok, A.; Ben-David, Y.; Milstein, D. J. Am. Chem. Soc. 1996, 118, 12406. (e) van der Boom, M. E.; Kraatz, H.-B.; Ben-David, Y.; Milstein, D. Chem. Commun. 1996, 2167. (f) Liou, Sh.-Y.; van der Boom, M. E.; Milstein, D. Chem. Commun. 1998, 687. (g) van der Boom, M. E.; Liou, Sh.-Y.; Ben-David, Y.; Gozin, M.; Milstein, D. J. Am. Chem. Soc. 1998, 120, 13415.
22. Gandelman, M.; Vigalok, A.; Shimon, L. J. W.; Milstein, D. Organonetallics 1997, 16, 3981.
23. Schrock, R. R.; Osborn, J. A. J. Am. Chem. Soc. 1971, 93, 3089.
24. 3). Elem. Anal. Found (Calcd) C 52.91 (51.77), H 7.74 (8.05).
25. Methylene chloride was added to increase the solubility of the reagents, which have limited solubility in acetonitrile.
26. Rh-H Elem. Anal. Found (Calcd) C 52.36 (52.55), H 7.75 (7.97).
27. In the isopropyl nitrile-methylene chloride system the products of C-H activation (complex 6) and C-C activation (complex 7) are analogous to those observed using acetonitrile-methylene chloride. For the characterization see Supporting Information.
28. 2 as a solvent.