Reaction of allylic and benzylic alcohols and esters with PPh3/I2: one-pot synthesis of β,γ-unsaturated compounds

The treatment of tertiary and secondary allylic alcohols containing a terminal double bond, and their acetyl derivatives, with triphenylphosphine and iodine under mild conditions leads regiospecifically and in high stereoselectivity to the corresponding primary allylic iodides, which can react ‘in situ’ with diverse nucleophiles. Primary allylic alcohols and benzyl alcohols and acetates are also transformed into the corresponding iodides under these conditions.