58352-81-1Relevant academic research and scientific papers
Development and comparison of the substrate scope of Pd-catalysts for the aerobic oxidation of alcohols
Schultz, Mitchell J.,Hamilton, Steven S.,Jensen, David R.,Sigman, Matthew S.
, p. 3343 - 3352 (2007/10/03)
(Chemical Equation Presented) 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(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°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 O2 source) but with a more limited substrate scope.
Benzyl trityl ether and DDQ as new tritylating reagents
Oikawa, Masato,Yoshizaki, Hiroaki,Kusumoto, Shoichi
, p. 757 - 760 (2007/10/03)
We describe herein a new tritylation procedure of alcohols using benzyl trityl ether and 2,3-dichloro-5,6-dicyano-1,4-benzoquinone. The reaction involves oxidative abstraction of one of the benzylic protons of benzyl trityl ether, followed by transformation of the generated benzyl trityl ether cation into a complex of benzaldehyde and trityl cation. The present procedure proceeds under mild neutral conditions to afford trityl ethers in generally good yields for primary alcohols, and in acceptable yields for several secondary alcohols.
