Mixed Surfactant Nano-Assemblies for Allylic Alcohol Etherification in Aqueous Medium

Abstract

Mixed nano-assemblies formed by two surfactants have rarely been used to catalyze organic reactions. In this study, nano-assemblies formed by SDS and CTAB were applied for the etherification of allylic alcohols with benzyl, aliphatic, and natural product alcohols at room temperature in an aqueous medium. In the presence of SDS-CTAB nano-assemblies and Brønsted acid catalyst pTSA, various allylic alcohols were reacted with different nonallylic alcohols to generate the desired ether products in moderate to good yields (62%–93%). SDS-CTAB nano-assemblies provide hydrophobic environments that effectively encapsulate both allylic alcohols and benzyl/aliphatic alcohols in their interiors. The anionic surface charge of these assemblies not only facilitates proton transfer from pTSA in the bulk solution to the allylic alcohol within the assemblies, but also stabilizes the allylic carbocation intermediates and localizes them on the surface. As a result, the reaction of allylic alcohols with nonallylic alcohols in the SDS-CTAB nano-assemblies increased both reaction rate and synthetic yields of the desired products by effectively suppressing two side reactions: reduction and self-etherification. This methodology provides an environmentally friendly approach for obtaining various allylic ether products. © 2025 Wiley-VCH GmbH.