Polymer-Supported Sulfinimidoyl Chlorides: A Convenient Reagent for Oxidation of Alcohols

Two polymer-supported sulfinimidoyl chlorides, i.e., 4-(N-tert-butylchlorosulfinimidoyl)phenoxymethylpolystyrene (3) and 4-(N-tert-butylchlorosulfinimidoyl) polystyrene (10), were prepared from chloromethylpolystyrene and polystyrene, respectively. Stoichiometric or catalytic oxidation of various primary and secondary alcohols using these polymer-supported sulfinimidoyl chlorides proceeded smoothly, and the corresponding aldehydes and ketones were conveniently prepared in good-to-high yields by simple work-up procedures. The polymer-supported oxidant 10 was recycled repeatedly by chlorination of a used polymer 11 with Nchlorosuccinimide (NCS) after stoichiometric oxidation.