Reversing the role of the metal - oxygen π-bond. Chemoselective catalytic reductions with a rhenium(V)-dioxo complex

Journal of the American Chemical Society

Volumn 125, Issue 14, 2003, Pages 4056-4057

  Kennedy Smith, Joshua J ^a   Nolin, Kristine A ^a   Gunterman, Haluna P ^a   Toste, F Dean ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BENZENE DERIVATIVE; ETHER DERIVATIVE; IODODIOXO(BISTRIPHENYLPHOSPHINE)RHENIUM; METAL; OXYGEN; RHENIUM COMPLEX; SILANE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL BOND; CHEMICAL STRUCTURE; COMPLEX FORMATION; ELECTRON TRANSPORT; ENANTIOSELECTIVITY; OXIDATION; REACTION ANALYSIS; REDUCTION; STRUCTURE ANALYSIS; TEMPERATURE DEPENDENCE;

EID: 0037427281     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja029498q     Document Type: Article

References (24)

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2. For several examples, see: Handbook of Reagents for Organic Synthesis: Oxidizing and Reducing Agents; Burke, S. D., Danheiser, R. L., Eds.; John Wiley & Sons: New York, 1999. Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: New York, 1991; Vol. 7. See also: Nugent, W. A.; Mayer, J. M. Metal-Ligand Multiple Bonds; Wiley: New York, 1988.
3. For several examples, see: Handbook of Reagents for Organic Synthesis: Oxidizing and Reducing Agents; Burke, S. D., Danheiser, R. L., Eds.; John Wiley & Sons: New York, 1999. Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: New York, 1991; Vol. 7. See also: Nugent, W. A.; Mayer, J. M. Metal-Ligand Multiple Bonds; Wiley: New York, 1988.
4. For a review of hydrosilylation, see: Ojima, I.; Li, Z.; Zhu, J. In The Chemistry of Organic Silicon Compounds; Rappoport, Z., Apelog, Y., Eds.; John Wiley & Sons: New York, 1998; Chapter 29. Vol. 2. Carpentier, J.-F.; Bette, V. Curr. Org. Chem. 2002, 6, 913.
5. For a review of hydrosilylation, see: Ojima, I.; Li, Z.; Zhu, J. In The Chemistry of Organic Silicon Compounds; Rappoport, Z., Apelog, Y., Eds.; John Wiley & Sons: New York, 1998; Chapter 29. Vol. 2. Carpentier, J.-F.; Bette, V. Curr. Org. Chem. 2002, 6, 913.
6. For some examples, see: V=O catalyzed acetylation of alcohols. Chen, C.-T.; Kuo, J.-H.; Li, C.-H.; Barhate, N. B.; Hon, S.-W.; Li, T.-W.; Chao, S.-D.; Liu, C.-C.; Li, Y.-C.; Chang, I.-H.; Lin, J.-S.; Liu, C.-J.; Chou, Y.-C. Org. Lett. 2001, 3, 3739. V=O catalyzed Diels - Alder. Togni, A. Organometallics 1990, 9, 3106. V=O catalyzed rearrangement-aldol of propargyl alcohols. Trost, B. M.; Oi, S. J. Am. Chem. Soc. 2001, 123, 1230. Re=O catalyzed olefination of aldehydes. Ledford, B. E.; Carreira, E. M. Tetrahedron Lett. 1997, 38, 8125.
7. For some examples, see: V=O catalyzed acetylation of alcohols. Chen, C.-T.; Kuo, J.-H.; Li, C.-H.; Barhate, N. B.; Hon, S.-W.; Li, T.-W.; Chao, S.-D.; Liu, C.-C.; Li, Y.-C.; Chang, I.-H.; Lin, J.-S.; Liu, C.-J.; Chou, Y.-C. Org. Lett. 2001, 3, 3739. V=O catalyzed Diels - Alder. Togni, A. Organometallics 1990, 9, 3106. V=O catalyzed rearrangement-aldol of propargyl alcohols. Trost, B. M.; Oi, S. J. Am. Chem. Soc. 2001, 123, 1230. Re=O catalyzed olefination of aldehydes. Ledford, B. E.; Carreira, E. M. Tetrahedron Lett. 1997, 38, 8125.
8. For some examples, see: V=O catalyzed acetylation of alcohols. Chen, C.-T.; Kuo, J.-H.; Li, C.-H.; Barhate, N. B.; Hon, S.-W.; Li, T.-W.; Chao, S.-D.; Liu, C.-C.; Li, Y.-C.; Chang, I.-H.; Lin, J.-S.; Liu, C.-J.; Chou, Y.-C. Org. Lett. 2001, 3, 3739. V=O catalyzed Diels - Alder. Togni, A. Organometallics 1990, 9, 3106. V=O catalyzed rearrangement-aldol of propargyl alcohols. Trost, B. M.; Oi, S. J. Am. Chem. Soc. 2001, 123, 1230. Re=O catalyzed olefination of aldehydes. Ledford, B. E.; Carreira, E. M. Tetrahedron Lett. 1997, 38, 8125.
9. For some examples, see: V=O catalyzed acetylation of alcohols. Chen, C.-T.; Kuo, J.-H.; Li, C.-H.; Barhate, N. B.; Hon, S.-W.; Li, T.-W.; Chao, S.-D.; Liu, C.-C.; Li, Y.-C.; Chang, I.-H.; Lin, J.-S.; Liu, C.-J.; Chou, Y.-C. Org. Lett. 2001, 3, 3739. V=O catalyzed Diels - Alder. Togni, A. Organometallics 1990, 9, 3106. V=O catalyzed rearrangement-aldol of propargyl alcohols. Trost, B. M.; Oi, S. J. Am. Chem. Soc. 2001, 123, 1230. Re=O catalyzed olefination of aldehydes. Ledford, B. E.; Carreira, E. M. Tetrahedron Lett. 1997, 38, 8125.
10. Addition of Si-H to Ti=S. Sweeney, Z. K.; Polse, J. L.; Andersen, R. A.; Bergman, R. G.; Kubinec, M. G. J. Am. Chem. Soc. 1997, 119, 4543. Sweeney, Z. K.; Polse, J. L.; Bergman, R. G.; Andersen, R. A. Organometallics 1999, 18, 5502. Addition of Si-H to Ta=N. Gountchev, T. I.; Tilley, T. D. J. Am. Chem. Soc. 1997, 117, 112831.
11. Addition of Si-H to Ti=S. Sweeney, Z. K.; Polse, J. L.; Andersen, R. A.; Bergman, R. G.; Kubinec, M. G. J. Am. Chem. Soc. 1997, 119, 4543. Sweeney, Z. K.; Polse, J. L.; Bergman, R. G.; Andersen, R. A. Organometallics 1999, 18, 5502. Addition of Si-H to Ta=N. Gountchev, T. I.; Tilley, T. D. J. Am. Chem. Soc. 1997, 117, 112831.
12. Addition of Si-H to Ti=S. Sweeney, Z. K.; Polse, J. L.; Andersen, R. A.; Bergman, R. G.; Kubinec, M. G. J. Am. Chem. Soc. 1997, 119, 4543. Sweeney, Z. K.; Polse, J. L.; Bergman, R. G.; Andersen, R. A. Organometallics 1999, 18, 5502. Addition of Si-H to Ta=N. Gountchev, T. I.; Tilley, T. D. J. Am. Chem. Soc. 1997, 117, 112831.
13. Rappé, A. K.; Goddard, W. A., III. J. Am Chem. Soc. 1982, 104, 448.
14. For the reaction of MTO with silanes, see: Tan, H.; Yoshikawa, A.; Gordon, M. S.; Espenson, J. Organometallics 1999, 18, 4753.
15. 1 is commercially available; however, we generally prepare it according to a modification (see Supporting Information) of: Ciani, G. F.; D'Allfonso, G.; Romtti, P. F.; Sironi, A.; Freni, M. Inorg. Chim. Acta 1983, 72, 29.
16. Competition experiments using 2 mol % 1 and p-nitrobenzaldehyde revealed the following order of reactivity: DMPS-H > TES-H > DPMS-H ≫ TBDMS-H.
17. Copper(+1) catalyzed hydrosilylation of cyclopropylphenyI ketone produces ring-opened product by a proposed single electron-transfer mechanism. Ito, H.; Yamanaka, H.; Ishizuka, T.; Tateiwa, J.; Hosomi, A. Synlett 2000, 479.
18. 7 failed to catalyze the hydrosilylation reaction.
19. A [3 + 2]-type addition of silane to O=Re=O is also possible: Collman, J. P.; Slaughter, L. M.; Eberspacher, T. A.; Strassner, T.; Brauman, J. I. Inorg. Chem. 2001, 40, 6272.
20. 3 signal appears between -0.42 and -0.54 ppm. Paulo, A.; Domingos, Â.; Garcia, R.; Santos, I. Inorg. Chem. 2000, 39, 5669. Reddy, K. R.; Domingos, A.; Paulo, A.; Santos, I. Inorg. Chem. 1999, 38, 4278.
21. 3 signal appears between -0.42 and -0.54 ppm. Paulo, A.; Domingos, Â.; Garcia, R.; Santos, I. Inorg. Chem. 2000, 39, 5669. Reddy, K. R.; Domingos, A.; Paulo, A.; Santos, I. Inorg. Chem. 1999, 38, 4278.
22. 1H NMR signal for the Re-H at 6.85 ppm: Matano, Y.; Brown, S. N.; Northcutt, T. O.; Mayer, J. M. Organometallics 1998, 17, 2939.
23. Reaction of a Re oxo-hydride with aldehydes, see ref 13.
24. Alternatively, intermolecular addition of a silane to 7 produces the silyl ether and regenerates 6.