Oxy-functionalization of nucleophilic rhenium(I) metal carbon bonds catalyzed by selenium(IV)

Journal of the American Chemical Society

Volumn 131, Issue 7, 2009, Pages 2466-2468

  Tenn, William J ^a   Conley, Brian L ^a   Hövelmann, Claas H ^c   Ahlquist, Märten ^b   Nielsen, Robert J ^b   Ess, Daniel H ^b,c   Oxgaard, Jonas ^b   Bischof, Steven M ^c   Goddard III, William A ^b   Periana, Roy A ^c  

^a UNIVERSITY OF SOUTHERN CALIFORNIA   (United States)

^b California Institute of Technology   (United States)

^c SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CARBON BOND; DFT CALCULATION; FUNCTIONALIZATION; MECHANISTIC STUDIES; METHYL GROUP; N-PROPYL; NEW STRATEGY; PRIMARY ALCOHOLS;

HYDROCARBONS; METHANOL; RHENIUM; SELENIUM; SELENIUM COMPOUNDS; SULFUR COMPOUNDS;

RHENIUM COMPOUNDS;

RHENIUM; SELENIUM;

ALKYLATION; ARTICLE; CATALYSIS; CHEMICAL BOND; OXIDATION; REACTION ANALYSIS;

EID: 67849090939     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja806814c     Document Type: Article

References (37)

1. Arndtsen, B. A.; Bergman, R. G.; Mobley, T. A.; Peterson, T. H. Acc. Chem. Res. 1995, 28, 154 and citations therein. (2) Crabtree, R. H. J. Organomet. Chem. 2004, 689, 4083.
2. (a) Shilov, A. E.; Shul'pin, G. B. Chem. Rev. 1997, 97, 2879.
3. (b) Periana, R. A.; Mironov, O.; Taube, D.; Bhalla, G.; Jones, C. Science 2003, 30, 814.
4. Lin, M.; Hogan, T.; Sen, A. J. Am. Chem. Soc. 1997, 119, 6048.
5. Muehlhofer, M.; Strassner, T.; Herrmann, W. A. Angew. Chem., Int. Ed. 2002, 41, 1745.
6. (a) Tenn, W. J., III.; Young, K. J. H.; Bhalla, G.; Oxgaard, J.; Goddard, W. A., III; Periana, R. A. J. Am. Chem. Soc. 2005, 127, 14172.
7. (b) Tenn, W. J., III; Young, K. J. H.; Oxgaard, J.; Nielsen, R. J.; Goddard, W. A., III; Periana, R. A. Organometallics 2006, 25, 5173.
8. (a) Klei, S. R.; Golden, J. T.; Tilley, D.; Bergman, R. G. J. Am. Chem. Soc. 2002, 124, 2092.
9. (b) Feng, Y.; Lail, M.; Barakat, K. A.; Cundari, T. R.; Gunnoe, T. B.; Petersen, J. L. J. Am. Chem. Soc. 2002, 127, 14174.
10. Kloek, S. M.; Heinekey, D. M.; Goldberg, K. I. Angew. Chem., Int. Ed. 2007, 46, 4736.
11. (a) Conley, B. L.; Ganesh, S. K.; Gonzales, J. M.; Tenn, W. J., III; Young, K. J. H.; Oxgaard, J.; Goddard, W. A., III; Periana, R. A. J. Am. Chem. Soc. 2006, 128, 9018.
12. (b) Conley, B.; Ganesh, S. K.; Gonzales, J. M.; Ess, D. H.; Nielsen, R. J.; Ziatdinov, V. R.; Oxgaard, J.; Goddard, W. A., III; Periana, R. A. Angew. Chem., Int. Ed. 2008, 41, 7849.
13. (a) Bibler, J. P.; Wojcicki, A. J. Am. Chem. Soc. 1964, 86, 5051.
14. (b) Wojcicki, A. Acc. Chem. Res. 1971, 4, 344. Lorenz, I.-P. Angew. Chem., Int. Ed. Engl. 1978, 17, 53.
15. Bird, L.; Challenger, F. J. Chem. Soc. 1942, 570.
16. (a) Sharpless, K. B.; Gordon, K. M. J. Am. Chem. Soc. 1976, 98, 300.
17. (b) Corey, E. J.; Schaefer, J. P. J. Am. Chem. Soc. 1960, 82, 918.
18. Selenium in Natural Products Synthesis, Nicolaou, K. C.; Petasis, N. A.; CIS; Philadelphia, 1984.
19. Sharpless, K. B.; Lauer, R. F. J. Am. Chem. Soc. 1972, 94, 7154.
20. (e) Umbreit, M. A.; Sharpless, K. B. J. Am. Chem. Soc. 1977, 99, 5526.
21. (a) Patel, B. M.; Price, G. L. Ind. Eng. Chem. Res. 1990, 29, 730.
22. (b) Mann, R. S.; Lao, K. C. Ind. Eng. Chem. Res. 1967, 6, 263.
23. Waitkins, G. R.; Clark, C. W. Chem. Rev. 1945, 36, 235.
24. Beck, W.; Raab, K.; Nagel, U.; Steinmann, M. Angew. Chem., Int. Ed. Engl. 1982, 21, 526.
25. (a) Lucia, L. A.; Burton, R. D.; Schanze, K. S. Inorg. Chim. Acta 1993, 208, 103.
26. (b) Worl, L. A.; Duesing, R.; Chen, P.; Della Ciana, L.; Meyer, T. J. J. Chem. Soc., Dalton Trans. 1991, 849.
27. Haas, A.; Schinkel, K. Chem. Ber. 1990, 123, 685.
28. (a) All calculations were performed using the B3LYP hybrid density functional as implemented in Jaguar 6.5 and 7.5. For all atoms except Se, the LACV3P** basis set was used for geometry optimizations and solvation energies, and LACV3P**++ for single-point gas phase energy corrections. For Se, the augmented MSV all electron basis set was used. See Supporting Information for details. (b) Jaguar, version 7.5; Schrodinger, LLC: New York, 2008.
29. We believe that part of the discrepancy between the experimental and theoretical activation enthalpy is due to the theoretical solvation model. This computes the free energy of solvation and therefore contains entropic contributions from solvent rearrangement.
30. There have been several recent examples of Re mediated C-H activation. For example:
31. (a) Kuninobu, Y.; Nishina, Y.; Matsuki, T.; Takai, K. J. Am. Chem. Soc. 2008, 130, 14062.
32. (b) Kuninobu, Y.; Nishina, Y.; Okaguchi, K.; Shouho, M.; Takai, K. Bull. Chem. Soc. Jpn. 2008, 81, 1393.
33. Kuninobu, Y.; Nishina, Y.; Nakagawa, C.; Takai, K. J. Am. Chem. Soc. 2006, 128, 12376.
34. Kuninobu, Y.; Nishina, Y.; Shouho, M.; Takai, K. Angew. Chem., Int. Ed. 2006, 45, 2766.
35. (e) Kuninobu, Y.; Tokunaga, Y.; Kawata, A.; Takai, K. J. Am. Chem. Soc. 2006, 128, 202.
36. (f) Kuninobu, Y.; Kawata, A.; Takai, K. J. Am. Chem. Soc. 2005, 127, 13498.
37. (g) Gonzales, J. M.; Oxgaard, J.; Periana, R. A.; Goddard, W. A., III. Organometallics 2007, 26, 1505.