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Highly chemoselective synthesis of aryl allylic sulfoxides through calcium hypobromite oxidation of aryl allylic sulfides |
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| Authors: | Vittorio Pace Laura CastoldiWolfgang Holzer |
| Affiliation: | a Department of Organic and Pharmaceutical Chemistry, Complutense University, Pza. Ramón y Cajal s/n, Madrid 28040, Spain b Department of Drug and Natural Product Synthesis, University of Vienna, Althanstrasse 14, Vienna 1090, Austria c Department of Pharmaceutical Chemistry, University of Pavia, Via Taramelli 12, 27100 Pavia, Italy |
| Abstract: | A highly chemoselective oxidation of widely substituted aryl allylic sulfides, prepared by allylation of arylthioethers with KF-Celite, to the corresponding aryl allylic sulfoxide was achieved by employing calcium hypobromite. Neither over-oxidation to sulfones nor halogenation of the aromatic rings was observed. The protocol may be successfully applied for the oxidation of substituted allylic systems (i.e., 2-haloallyl) that per se could interact with the oxidizing agent. |
| Keywords: | Sulfoxides Allylic compounds Chemoselectivity Hypohalites KF-Celite |
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