Tandem oxidation/halogenation of aryl allylic alcohols under Moffatt-Swern conditions.
Aryl allylic alcohols are converted to halogenated unsaturated ketones or allylic halides using excess Moffatt-Swern reagent. Electron-poor aromatic rings favor formation of the halogenated ketone, while electron-donating substituents in the ortho or para positions favor formation of the allylic halide. The oxidation/halogenation reaction performs well with both oxalyl chloride and oxalyl bromide, providing access to the corresponding chlorides or bromides, respectively.
Yin
Jiandong
J
Department of Chemistry, 1-014 Center for Science and Technology, Syracuse University, Syracuse, New York 13244, USA.
Gallis
Christina E
CE
Chisholm
John D
JD