Development and Comparison of the Substrate Scope of Pd-Catalysts for the Aerobic Oxidation of Alcohols
| Autor: | Mitchell J. Schultz, Matthew S. Sigman, Steven S. Hamilton, David R. Jensen |
|---|---|
| Rok vydání: | 2005 |
| Předmět: |
inorganic chemicals
Allylic rearrangement Diol chemistry.chemical_element Alcohol Catalysis Article chemistry.chemical_compound Organic chemistry heterocyclic compounds Triethylamine Molecular Structure organic chemicals Organic Chemistry Temperature Substrate (chemistry) General Medicine Kinetics chemistry Alcohols Alcohol oxidation Palladium(II) acetate Aliphatic compound Oxidation-Reduction Palladium |
| Zdroj: | ChemInform. 36 |
| ISSN: | 1522-2667 0931-7597 |
| DOI: | 10.1002/chin.200539045 |
| Popis: | [reaction: see text] Three catalysts for aerobic oxidation of alcohols are discussed and the effectiveness of each is evaluated for allylic, benzylic, aliphatic, and functionalized alcohols. Additionally, chiral nonracemic substrates as well as chemoselective and diastereoselective oxidations are investigated. In this study, the most convenient system for the Pd-catalyzed aerobic oxidation of alcohols is Pd(OAc)(2) in combination with triethylamine. This system functions effectively for the majority of alcohols tested and uses mild conditions (3 to 5 mol % of catalyst, room temperature). Pd(IiPr)(OAc)(2)(H(2)O) (1) also successfully oxidizes the majority of alcohols evaluated. This system has the advantage of significantly lowering catalyst loadings but requires higher temperatures (0.1 to 1 mol % of catalyst, 60 degrees C). A new catalyst is also disclosed, Pd(IiPr)(OPiv)(2) (2). This catalyst operates under very mild conditions (1 mol %, room temperature, and air as the O(2) source) but with a more limited substrate scope. |
| Databáze: | OpenAIRE |
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