Abstract
Titanium sites grafted on several siliceous supports are able to act as multifunctional catalytic centers, activating tert-butyl hydroperoxide for oxidation reactions, as redox centers, and promoting rearrangements, as Lewis acids. In the one-pot, four-step conversion of stilbene into benzophenone, the best results were obtained over Ti-MCM41. Under suitable conditions, the catalyst promotes a tandem sequence: alkene epoxidation, epoxide rearrangement, aldehyde oxidation, and oxidative decarboxylation. α,α,α-Trifluorotoluene and a fluorinated glycerol-derived solvent were the optimal solvents for this tandem process, due to their polar aprotic character that allows the efficient oxidation reactions and a poor coordinating ability to prevent any deactivation of the Lewis acid character of the sites. The result of the tandem sequence of reactions is a ketone with loss of a carbon atom that, depending on the starting alkene, is the same result as that of an ozonolysis but under safer and milder conditions. I...
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