Highly selective oxidation of allylic alcohols to α,β-unsaturated aldehydes using Pd cluster catalysts in the presence of molecular oxygen

Journal of Organic Chemistry

Volumn 61, Issue 14, 1996, Pages 4502-4503

  Kaneda, Kiyotomi ^a   Fujii, Masanori ^a   Morioka, Kengo ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000629671     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9605307     Document Type: Article

References (33)

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15. 3c
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26. 2: Lansbury, P. T.; Hangauer, D. G.; Vacca, J. P. J. Am. Chem. Soc. 1980, 102, 3964. Generally, effective reagents for the selective oxidation of allylic alcohols also give high activity for oxidation of benzylic alcohols. However, benzyl alcohol was not readily oxidized to benzaldehyde (16% for 48 h) under the present reaction conditions.
27. 2: Lansbury, P. T.; Hangauer, D. G.; Vacca, J. P. J. Am. Chem. Soc. 1980, 102, 3964. Generally, effective reagents for the selective oxidation of allylic alcohols also give high activity for oxidation of benzylic alcohols. However, benzyl alcohol was not readily oxidized to benzaldehyde (16% for 48 h) under the present reaction conditions.
28. 2: Lansbury, P. T.; Hangauer, D. G.; Vacca, J. P. J. Am. Chem. Soc. 1980, 102, 3964. Generally, effective reagents for the selective oxidation of allylic alcohols also give high activity for oxidation of benzylic alcohols. However, benzyl alcohol was not readily oxidized to benzaldehyde (16% for 48 h) under the present reaction conditions.
29. 2: Lansbury, P. T.; Hangauer, D. G.; Vacca, J. P. J. Am. Chem. Soc. 1980, 102, 3964. Generally, effective reagents for the selective oxidation of allylic alcohols also give high activity for oxidation of benzylic alcohols. However, benzyl alcohol was not readily oxidized to benzaldehyde (16% for 48 h) under the present reaction conditions.
30. Using a mixed solvent of benzene and AcOH could depress the esterification and hydrogenation to give high yields of the α,β-unsaturated aldehydes (run 12 in Table 2).
31. For reviews of the mechanism of alcohol oxidations see: (a) Simandi, L. I. Catalytic Activation of Dioxygen by Metal Complexes; Kluwer Academic Publishers: Netherlands, 1992. (b) Hudlicky, M. Oxidations in Organic Chemistry; ACS Monograph: Washington, DC, 1990. (c) Sheldon, R. A.; Kochi, J. K. Metal-Catalyzed Oxidations of Organic Compounds; Academic Press: London, 1981.
32. For reviews of the mechanism of alcohol oxidations see: (a) Simandi, L. I. Catalytic Activation of Dioxygen by Metal Complexes; Kluwer Academic Publishers: Netherlands, 1992. (b) Hudlicky, M. Oxidations in Organic Chemistry; ACS Monograph: Washington, DC, 1990. (c) Sheldon, R. A.; Kochi, J. K. Metal-Catalyzed Oxidations of Organic Compounds; Academic Press: London, 1981.
33. For reviews of the mechanism of alcohol oxidations see: (a) Simandi, L. I. Catalytic Activation of Dioxygen by Metal Complexes; Kluwer Academic Publishers: Netherlands, 1992. (b) Hudlicky, M. Oxidations in Organic Chemistry; ACS Monograph: Washington, DC, 1990. (c) Sheldon, R. A.; Kochi, J. K. Metal-Catalyzed Oxidations of Organic Compounds; Academic Press: London, 1981.