Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 70, Issue 9, Pages 3343-3352Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo0482211
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Funding
- NIGMS NIH HHS [R01 GM063540, R01 GM063540-05, R01 GM63540] Funding Source: Medline
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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(CAc)(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(H2O) (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.
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