A bimetallic system for the catalytic hydroxylation of remote primary C- H bonds in functionalized organics using dioxygen

Journal of the American Chemical Society

Volumn 122, Issue 17, 2000, Pages 4029-4031

  Shen, Chengyu ^a   Garcia Zayas, Eduardo A ^a   Sen, Ayusman ^a  

^a PENNSYLVANIA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACID; ALCOHOL; CARBON MONOXIDE; COPPER CHLORIDE; HALIDE; HYDROGEN PEROXIDE; METAL; OXYGEN; PALLADIUM; PROPIONIC ACID; TRIFLUOROACETIC ACID; WATER;

ARTICLE; CATALYSIS; CHEMICAL BINDING; CONCENTRATION RESPONSE; HYDROXYLATION; OXIDATION; REACTION ANALYSIS;

EID: 0034600302     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja993457l     Document Type: Article

References (21)

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2. Recent reviews: (a) Sen, A. Acc. Chem. Res. 1998, 31, 550. (b) Stahl, S. S.; Labinger, J. A.; Bercaw, J. E. Angew. Chem., Int. Ed. 1998, 37, 2181. (c) Jones, W. D. Top. Organomet. Chem. 1999, 3, 9. (d) Kakiuchi, F.; Murai, S. Top. Organomet. Chem. 1999, 3, 47. (e) Sen, A. Top. Organomet. Chem. 1999, 3, 81. (f) Sen, A. In Applied Homogeneous Catalysis with Organometallic Compounds; Hermann, W. A., Cornils, B., Eds.; VCH: Weinheim, 1996; Vol. 2, p 1081. (g) Crabtree, R. H. Chem. Rev. 1995, 95, 987. (h) Arndtsen, B. A.; Bergman, R. G.; Mobley, T. A.; Peterson, T. H. Acc. Chem. Res. 1995, 28, 154. (i) Labinger, J. A. Fuel Process. Technol. 1995, 42, 325. (j) Hall, T. J.; Hargreaves, J. S. J.; Huchings, G. J.; Joyner, R. W.; Taylor, S. H. Fuel Process. Technol. 1995, 42, 151. (k) Olah, G. A.; Molnár, A. Hydrocarbon Chemistry; Wiley: New York, 1995. (l) Also see: Liu, F.; Pak, E. B.; Singh, B.; Jensen, C. M.; Goldman, A. S. J. Am. Chem. Soc. 1999, 121, 4086.
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4. Recent reviews: (a) Sen, A. Acc. Chem. Res. 1998, 31, 550. (b) Stahl, S. S.; Labinger, J. A.; Bercaw, J. E. Angew. Chem., Int. Ed. 1998, 37, 2181. (c) Jones, W. D. Top. Organomet. Chem. 1999, 3, 9. (d) Kakiuchi, F.; Murai, S. Top. Organomet. Chem. 1999, 3, 47. (e) Sen, A. Top. Organomet. Chem. 1999, 3, 81. (f) Sen, A. In Applied Homogeneous Catalysis with Organometallic Compounds; Hermann, W. A., Cornils, B., Eds.; VCH: Weinheim, 1996; Vol. 2, p 1081. (g) Crabtree, R. H. Chem. Rev. 1995, 95, 987. (h) Arndtsen, B. A.; Bergman, R. G.; Mobley, T. A.; Peterson, T. H. Acc. Chem. Res. 1995, 28, 154. (i) Labinger, J. A. Fuel Process. Technol. 1995, 42, 325. (j) Hall, T. J.; Hargreaves, J. S. J.; Huchings, G. J.; Joyner, R. W.; Taylor, S. H. Fuel Process. Technol. 1995, 42, 151. (k) Olah, G. A.; Molnár, A. Hydrocarbon Chemistry; Wiley: New York, 1995. (l) Also see: Liu, F.; Pak, E. B.; Singh, B.; Jensen, C. M.; Goldman, A. S. J. Am. Chem. Soc. 1999, 121, 4086.
5. Recent reviews: (a) Sen, A. Acc. Chem. Res. 1998, 31, 550. (b) Stahl, S. S.; Labinger, J. A.; Bercaw, J. E. Angew. Chem., Int. Ed. 1998, 37, 2181. (c) Jones, W. D. Top. Organomet. Chem. 1999, 3, 9. (d) Kakiuchi, F.; Murai, S. Top. Organomet. Chem. 1999, 3, 47. (e) Sen, A. Top. Organomet. Chem. 1999, 3, 81. (f) Sen, A. In Applied Homogeneous Catalysis with Organometallic Compounds; Hermann, W. A., Cornils, B., Eds.; VCH: Weinheim, 1996; Vol. 2, p 1081. (g) Crabtree, R. H. Chem. Rev. 1995, 95, 987. (h) Arndtsen, B. A.; Bergman, R. G.; Mobley, T. A.; Peterson, T. H. Acc. Chem. Res. 1995, 28, 154. (i) Labinger, J. A. Fuel Process. Technol. 1995, 42, 325. (j) Hall, T. J.; Hargreaves, J. S. J.; Huchings, G. J.; Joyner, R. W.; Taylor, S. H. Fuel Process. Technol. 1995, 42, 151. (k) Olah, G. A.; Molnár, A. Hydrocarbon Chemistry; Wiley: New York, 1995. (l) Also see: Liu, F.; Pak, E. B.; Singh, B.; Jensen, C. M.; Goldman, A. S. J. Am. Chem. Soc. 1999, 121, 4086.
6. Recent reviews: (a) Sen, A. Acc. Chem. Res. 1998, 31, 550. (b) Stahl, S. S.; Labinger, J. A.; Bercaw, J. E. Angew. Chem., Int. Ed. 1998, 37, 2181. (c) Jones, W. D. Top. Organomet. Chem. 1999, 3, 9. (d) Kakiuchi, F.; Murai, S. Top. Organomet. Chem. 1999, 3, 47. (e) Sen, A. Top. Organomet. Chem. 1999, 3, 81. (f) Sen, A. In Applied Homogeneous Catalysis with Organometallic Compounds; Hermann, W. A., Cornils, B., Eds.; VCH: Weinheim, 1996; Vol. 2, p 1081. (g) Crabtree, R. H. Chem. Rev. 1995, 95, 987. (h) Arndtsen, B. A.; Bergman, R. G.; Mobley, T. A.; Peterson, T. H. Acc. Chem. Res. 1995, 28, 154. (i) Labinger, J. A. Fuel Process. Technol. 1995, 42, 325. (j) Hall, T. J.; Hargreaves, J. S. J.; Huchings, G. J.; Joyner, R. W.; Taylor, S. H. Fuel Process. Technol. 1995, 42, 151. (k) Olah, G. A.; Molnár, A. Hydrocarbon Chemistry; Wiley: New York, 1995. (l) Also see: Liu, F.; Pak, E. B.; Singh, B.; Jensen, C. M.; Goldman, A. S. J. Am. Chem. Soc. 1999, 121, 4086.
7. Recent reviews: (a) Sen, A. Acc. Chem. Res. 1998, 31, 550. (b) Stahl, S. S.; Labinger, J. A.; Bercaw, J. E. Angew. Chem., Int. Ed. 1998, 37, 2181. (c) Jones, W. D. Top. Organomet. Chem. 1999, 3, 9. (d) Kakiuchi, F.; Murai, S. Top. Organomet. Chem. 1999, 3, 47. (e) Sen, A. Top. Organomet. Chem. 1999, 3, 81. (f) Sen, A. In Applied Homogeneous Catalysis with Organometallic Compounds; Hermann, W. A., Cornils, B., Eds.; VCH: Weinheim, 1996; Vol. 2, p 1081. (g) Crabtree, R. H. Chem. Rev. 1995, 95, 987. (h) Arndtsen, B. A.; Bergman, R. G.; Mobley, T. A.; Peterson, T. H. Acc. Chem. Res. 1995, 28, 154. (i) Labinger, J. A. Fuel Process. Technol. 1995, 42, 325. (j) Hall, T. J.; Hargreaves, J. S. J.; Huchings, G. J.; Joyner, R. W.; Taylor, S. H. Fuel Process. Technol. 1995, 42, 151. (k) Olah, G. A.; Molnár, A. Hydrocarbon Chemistry; Wiley: New York, 1995. (l) Also see: Liu, F.; Pak, E. B.; Singh, B.; Jensen, C. M.; Goldman, A. S. J. Am. Chem. Soc. 1999, 121, 4086.
8. Recent reviews: (a) Sen, A. Acc. Chem. Res. 1998, 31, 550. (b) Stahl, S. S.; Labinger, J. A.; Bercaw, J. E. Angew. Chem., Int. Ed. 1998, 37, 2181. (c) Jones, W. D. Top. Organomet. Chem. 1999, 3, 9. (d) Kakiuchi, F.; Murai, S. Top. Organomet. Chem. 1999, 3, 47. (e) Sen, A. Top. Organomet. Chem. 1999, 3, 81. (f) Sen, A. In Applied Homogeneous Catalysis with Organometallic Compounds; Hermann, W. A., Cornils, B., Eds.; VCH: Weinheim, 1996; Vol. 2, p 1081. (g) Crabtree, R. H. Chem. Rev. 1995, 95, 987. (h) Arndtsen, B. A.; Bergman, R. G.; Mobley, T. A.; Peterson, T. H. Acc. Chem. Res. 1995, 28, 154. (i) Labinger, J. A. Fuel Process. Technol. 1995, 42, 325. (j) Hall, T. J.; Hargreaves, J. S. J.; Huchings, G. J.; Joyner, R. W.; Taylor, S. H. Fuel Process. Technol. 1995, 42, 151. (k) Olah, G. A.; Molnár, A. Hydrocarbon Chemistry; Wiley: New York, 1995. (l) Also see: Liu, F.; Pak, E. B.; Singh, B.; Jensen, C. M.; Goldman, A. S. J. Am. Chem. Soc. 1999, 121, 4086.
9. Recent reviews: (a) Sen, A. Acc. Chem. Res. 1998, 31, 550. (b) Stahl, S. S.; Labinger, J. A.; Bercaw, J. E. Angew. Chem., Int. Ed. 1998, 37, 2181. (c) Jones, W. D. Top. Organomet. Chem. 1999, 3, 9. (d) Kakiuchi, F.; Murai, S. Top. Organomet. Chem. 1999, 3, 47. (e) Sen, A. Top. Organomet. Chem. 1999, 3, 81. (f) Sen, A. In Applied Homogeneous Catalysis with Organometallic Compounds; Hermann, W. A., Cornils, B., Eds.; VCH: Weinheim, 1996; Vol. 2, p 1081. (g) Crabtree, R. H. Chem. Rev. 1995, 95, 987. (h) Arndtsen, B. A.; Bergman, R. G.; Mobley, T. A.; Peterson, T. H. Acc. Chem. Res. 1995, 28, 154. (i) Labinger, J. A. Fuel Process. Technol. 1995, 42, 325. (j) Hall, T. J.; Hargreaves, J. S. J.; Huchings, G. J.; Joyner, R. W.; Taylor, S. H. Fuel Process. Technol. 1995, 42, 151. (k) Olah, G. A.; Molnár, A. Hydrocarbon Chemistry; Wiley: New York, 1995. (l) Also see: Liu, F.; Pak, E. B.; Singh, B.; Jensen, C. M.; Goldman, A. S. J. Am. Chem. Soc. 1999, 121, 4086.
10. Recent reviews: (a) Sen, A. Acc. Chem. Res. 1998, 31, 550. (b) Stahl, S. S.; Labinger, J. A.; Bercaw, J. E. Angew. Chem., Int. Ed. 1998, 37, 2181. (c) Jones, W. D. Top. Organomet. Chem. 1999, 3, 9. (d) Kakiuchi, F.; Murai, S. Top. Organomet. Chem. 1999, 3, 47. (e) Sen, A. Top. Organomet. Chem. 1999, 3, 81. (f) Sen, A. In Applied Homogeneous Catalysis with Organometallic Compounds; Hermann, W. A., Cornils, B., Eds.; VCH: Weinheim, 1996; Vol. 2, p 1081. (g) Crabtree, R. H. Chem. Rev. 1995, 95, 987. (h) Arndtsen, B. A.; Bergman, R. G.; Mobley, T. A.; Peterson, T. H. Acc. Chem. Res. 1995, 28, 154. (i) Labinger, J. A. Fuel Process. Technol. 1995, 42, 325. (j) Hall, T. J.; Hargreaves, J. S. J.; Huchings, G. J.; Joyner, R. W.; Taylor, S. H. Fuel Process. Technol. 1995, 42, 151. (k) Olah, G. A.; Molnár, A. Hydrocarbon Chemistry; Wiley: New York, 1995. (l) Also see: Liu, F.; Pak, E. B.; Singh, B.; Jensen, C. M.; Goldman, A. S. J. Am. Chem. Soc. 1999, 121, 4086.
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12. Recent reviews: (a) Sen, A. Acc. Chem. Res. 1998, 31, 550. (b) Stahl, S. S.; Labinger, J. A.; Bercaw, J. E. Angew. Chem., Int. Ed. 1998, 37, 2181. (c) Jones, W. D. Top. Organomet. Chem. 1999, 3, 9. (d) Kakiuchi, F.; Murai, S. Top. Organomet. Chem. 1999, 3, 47. (e) Sen, A. Top. Organomet. Chem. 1999, 3, 81. (f) Sen, A. In Applied Homogeneous Catalysis with Organometallic Compounds; Hermann, W. A., Cornils, B., Eds.; VCH: Weinheim, 1996; Vol. 2, p 1081. (g) Crabtree, R. H. Chem. Rev. 1995, 95, 987. (h) Arndtsen, B. A.; Bergman, R. G.; Mobley, T. A.; Peterson, T. H. Acc. Chem. Res. 1995, 28, 154. (i) Labinger, J. A. Fuel Process. Technol. 1995, 42, 325. (j) Hall, T. J.; Hargreaves, J. S. J.; Huchings, G. J.; Joyner, R. W.; Taylor, S. H. Fuel Process. Technol. 1995, 42, 151. (k) Olah, G. A.; Molnár, A. Hydrocarbon Chemistry; Wiley: New York, 1995. (l) Also see: Liu, F.; Pak, E. B.; Singh, B.; Jensen, C. M.; Goldman, A. S. J. Am. Chem. Soc. 1999, 121, 4086.
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18. The formation of hydrogen peroxide through palladium-catalyzed reaction between carbon monoxide, water, and dioxygen has been the subject of several recent reports: (a) Bianchi, D.; Bortolo, R.; D'Aloisio, R.; Ricci, M. Angew. Chem., Int. Ed. 1999, 38, 706. (b) Rossella, B.; D'Aloisio, R.; Bianchi, D. European Patent Application, EP 788,998, 1997. (c) Bianchi, D.; Rossella, B.; D'Aloisio, R.; Ricci, M.; Soattini, S. European Patent Application, EP 808,796 A1, 1997.
19. The formation of hydrogen peroxide through palladium-catalyzed reaction between carbon monoxide, water, and dioxygen has been the subject of several recent reports: (a) Bianchi, D.; Bortolo, R.; D'Aloisio, R.; Ricci, M. Angew. Chem., Int. Ed. 1999, 38, 706. (b) Rossella, B.; D'Aloisio, R.; Bianchi, D. European Patent Application, EP 788,998, 1997. (c) Bianchi, D.; Rossella, B.; D'Aloisio, R.; Ricci, M.; Soattini, S. European Patent Application, EP 808,796 A1, 1997.
20. The formation of hydrogen peroxide through palladium-catalyzed reaction between carbon monoxide, water, and dioxygen has been the subject of several recent reports: (a) Bianchi, D.; Bortolo, R.; D'Aloisio, R.; Ricci, M. Angew. Chem., Int. Ed. 1999, 38, 706. (b) Rossella, B.; D'Aloisio, R.; Bianchi, D. European Patent Application, EP 788,998, 1997. (c) Bianchi, D.; Rossella, B.; D'Aloisio, R.; Ricci, M.; Soattini, S. European Patent Application, EP 808,796 A1, 1997.
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