Cyclometalation reactions on rhodium(I). Evidence for a chelate effect and competing C-H and C-O oxidative additions

Organometallics

Volumn 20, Issue 23, 2001, Pages 4919-4926

  Sjövall, Sven ^a   Andersson, Carlaxel ^a   Wendt, Ola F ^a  

^a LUND UNIVERSITY   (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

BISDIPHENYLPHOSPHINOBUTANE NORBORNADIENE RHODIUM TETRAFLUOROBORATE; BISDIPHENYLPHOSPHINOETHANE NORBORDIENE RHODIUM TETRAFLUOROBORATE; CHELATE EFFECT; CYCLOMETALATION REACTIONS; OXIDATIVE ADDITIONS; PHOSPHINE FUNCTIONALITIES; RHODIUM BENZYL HYDRIDE STEREOISOMERS; XRAY CRYSTALLOGRAPHY;

ADDITION REACTIONS; ATOMS; CHEMICAL ACTIVATION; COMPLEXATION; CRYSTAL STRUCTURE; HYDROGEN BONDS; ISOMERS; MOLECULAR STRUCTURE; OXIDATION; OXYGEN; REACTION KINETICS; X RAY ANALYSIS;

RHODIUM COMPOUNDS;

EID: 0035851939     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om010543x     Document Type: Article

References (51)

1. (a) Crabtree, R. H. Angew. Chem., Int. Ed. Engl. 1993, 32, 789.
2. (b) Crabtree, R. H. Chem. Rev. 1985, 85, 245.
3. (a) Arndtsen, B. A.; Bergman, R. G.; Mobley, T. A.; Peterson, T. H. Acc. Chem. Res. 1995, 28, 154.
4. (b) Canty, A. J.; van Koten, G. Acc. Chem. Res. 1995, 28, 406.
5. (c) Schneider, J. J. Angew. Chem., Int. Ed. Engl. 1996, 35, 1068.
6. (d) Ryabov, A. D. Chem. Rev. 1990, 90, 403.
7. (e) Stahl, S.; Labinger, J. A.; Bercaw, J. E. Angew. Chem., Int. Ed. Engl. 1998, 37, 2181.
8. Rybtchinski, B.; Milstein, D. Angew. Chem., Int. Ed. 1999, 38, 870.
9. (a) Cassar, L.; Halpern, J. J. Chem. Soc. D 1970, 1082.
10. (b) Cassar, L.; Eaton, P. E.; Halpern, J. J. Am. Chem. Soc. 1970, 92, 3515.
11. (c) Periana, R. A.; Bergman, R. G. J. Am. Chem. Soc. 1986, 108, 7346.
12. (d) Eilbracht, P. Chem. Ber. 1980, 113, 542.
13. (e) Urbanos, F.; Halcrow, M. A.; Fernandez-Baeza, J.; Dahan, F.; Labroue, D.; Chaudret, B. J. Am. Chem. Soc. 1993, 115, 3484.
14. (f) 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.
15. (g) Nicholls, J. C.; Spencer, J. L. Organometallics 1994, 13, 1781.
16. (h) Ingman, S. L.; Johnson, B. F. G.; Martin, C. M.; Parker, D. G. J. Chem. Soc., Chem. Commun. 1995, 159.
17. (i) Brown, D. B.; Dyson, P. J.; Johnson, B. F. G.; Martin, C. M.; Parker, D. G.; Parsons, S. J. Chem. Soc., Dalton Trans. 1997, 1909.
18. (j) Rybtchinski, B.; Vigalok, A.; Yehoshoa, B.-D.; Milstein, D. J. Am. Chem. Soc. 1996, 118, 12406.
19. (k) Gandelman, M.; Vigalok, A.; Shimon, L. J. W.; Milstein, D. Organometallics 1997, 16, 3981.
20. (a) Lewis, L. J. Am. Chem. Soc. 1986, 108, 743.
21. (b) Bergbreiter, D. E.; Osburn, P. L.; Liu, Y.-S. J. Am. Chem. Soc. 1999, 121, 9531.
22. (c) Donkervoort, J. G.; Vicario, G. L.; Jastrzebski, J. T. B. H.; Gossage, R. A.; Cahiez, G.; van Koten, G. J. Organomet. Chem. 1998, 558, 61.
23. (d) Beletskaya, I. P.; Cheprakov, A. V. Chem. Rev. 2000, 100, 3009.
24. (e) Steenwinkel, P.; Gossage, R. A.; van Koten, G. Chem. Eur. J. 1998, 4, 759.
25. (a) Sjövall, S.; Kloo, L.; Nikitidis, A.; Andersson, C. Organometallics 1998, 17, 579.
26. (b) Sjövall, S.; Johansson, M.; Andersson, C. Organometallics 1999, 18, 2198.
27. (c) Sjövall, S.; Svensson, P. H.; Andersson, C. Organometallics 1999, 18, 8, 5412.
28. (a) Zhang, L.; Zetterberg, K. Organometallics 1991, 10, 3806.
29. (b) Rybtchinski, B.; Konstantinovsky, L.; Shimon, L. J. W.; Vigalok, A.; Milstein, D. Chem. Eur. J. 2000, 6, 3287.
30. Nikitidis, A.; Andersson, C. Phosphorus, Sulfur Silicon Relat. Elem. 1993, 78, 141.
31. del Rio, I.; Ruiz, N.; Claver, C.; van der Veen, L. A.; van Leuween, P. W. N. M. J. Mol. Catal. A 2000, 161, 39.
32. Depuy, C. H.; King, R. W. Chem. Rev. 1960, 60, 431.
33. McNamara, B. K.; Yeston, J. S.; Bergman, R. G.; Moore, C. B. J. Am. Chem. Soc. 1999, 121, 6437.
34. (a) Yamamoto, A. Adv. Organomet. Chem. 1992, 34, 111.
35. (b) Nagayama, K.; Shimizu, I.; Yamamoto, A. Bull. Chem. Soc. Jpn. 1999, 72, 799.
36. 4] as the precursor gave the same thermolysis reaction as the corresponding DPPE complex, although at a higher rate.
37. (a) Garrou, P. E. Chem. Rev. 1981, 81, 229.
38. (b) Lindner, E.; Fawzi, R.; Mayer, H. A.; Eichele, K.; Hiller, W. Organometallics 1992, 11, 1033.
39. (a) Gill, D. F.; Shaw, B. L. J. Chem. Soc., Chem. Commun. 1972, 65.
40. (b) Crocker, C.; Errington, R. J.; Markham, R.; Moulton, C. J.; Odell, K. J.; Shaw, B. L. J. Am. Chem. Soc. 1980, 102, 4373.
41. Appleton, T. G.; Clark, H. C.; Manzer, L. E. Coord. Chem. Rev. 1973, 10, 335.
42. Brandenburg, K., DIAMOND, Program for Molecular Graphics; Crystal Impact, Bonn, Germany, 2000.
43. Crabtree, R. H.; Holt, E. M.; Lavin, M.; Morehouse, S. M. Inorg. Chem. 1985, 24, 1986.
44. Costain, C. C.; Stoicheff, B. P. J. Chem. Phys. 1959, 30, 777.
45. Fairlie, D. P.; Bosnich, B. Organometallics 1988, 7, 936.
46. Uson, R.; Oro, L. A.; Garralda, M. A.; Claver, M. C.; Lahuerta, P. Transition Met. Chem. 1979, 4, 55.
47. Schiemenz, G.; Kaack, H. Liebigs Ann. Chem. 1973, 1494.
48. BrukerAXS, SMART, Area Detector Control Software; Bruker Analytical X-ray Systems, Madison, WI, 1995.
49. Sheldrick, G. M. SADABS, Program for Absorption Correction; University of Göttingen, Göttingen, Germany, 1996.
50. BrukerAXS, SAINT, Integration Software; Bruker Analytical X-ray Systems, Madison, WI, 1995.
51. Sheldrick, G. M. SHELXTL5.1, Program for Structure Solution and Least Squares Refinement; University of Göttingen, Göttingen, Germany, 1998.