Deoxygenation of Sulfoxides to Sulfides with Thionyl Chloride and Triphenylphosphine: Competition with the Pummerer Reaction

Although a number of methods have been developed to reduce sulfoxides to sulfides, many of these processes are limited by side reactions, low yields, poorly available reagents, or harsh reaction conditions. We recently studied the reaction of various sulfoxides with SOCl2 and Ph3P. We were able to obtain the corresponding sulfides in excellent yields (>90%) when aliphatic and aromatic sulfoxides were treated with SOCl2 as a catalyst and Ph3P in THF at room temperature.