Oxone-Mediated Regioselective Oxy-iodination of 1-Aryl/Alkyl Butadienes Using TBAI.

A simple, mild, and environmentally benign regioselective oxy-iodination of 1-aryl/alkyl butadienes has been developed. While styrenes have been explored previously, this work on dienes has been highly regioselective and metal-free in oxy-iodination following Markovnikov's rule. The oxy-iodination products were obtained in good to excellent yields using various co-solvents (H 2 O, MeOH, EtOH, AcOH, etc.). In addition, the halohydrins have been useful building blocks in the synthesis of various functionalized keto iodides and azido alcohols.