Reactivity of Styrenes in Micelles: Safe, Selective, and Sustainable Functionalization with Azides and Carboxylic Acids

An amphiphile PS-750-M that mimics dipolar-aprotic organic solvents enables N-bromo succinimide (NBS)-mediated one-pot oxyfunctionalization of styrenes in water under mild conditions. Control experiments reveal the involvement of the radical pathway. The radical intermediate was also trapped with butylated hydroxytoluene to obtain a peroxy educt. The method is scalable without involving any operational risk. This aqueous micellar technology for oxyfunctionalization is further applied on in situ reduction and click chemistry to obtain β-azido alcohols and β-carbonyl triazoles.