Efficient Chemoselective Oxidation of Phenylmethanols to Aldehydes with Iodosobenzene

Primary phenylmethanols are selectively and efficiently oxidized to the corresponding aldehydes by the system C6H5IO/(C6H5)4PBr/CH2Cl2, T = 298 K under aerobic conditions. The use of the relatively stable iodosobenzene, an iodine(III) compound, in place of the usually employed and potentially explosive iodine(V) reagents, the easy work-up procedure, and the facile recycling of solvent and oxidant provides a convenient and environmentally benign oxidation method.