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 p TSA, 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 p TSA 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.

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Publication Details

Journal
Asian Journal of Organic Chemistry
Published
2025-03-27
DOI
https://doi.org/10.1002/ajoc.202500053
Citations
2
Primary Topic
Surfactants and Colloidal Systems
Type
article
Field-Weighted Citation Impact
1.87
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article

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

Pil Seok Chae, Waqar Ahmed, Hyun Sung Lee
2 citations
Asian Journal of Organic Chemistry
Surfactants and Colloidal Systems
1.87
article

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

Pil Seok Chae, Waqar Ahmed, Hyun Sung Lee
article en
2 citations

Abstract

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 p TSA, 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 p TSA 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.

Asian Journal of Organic ChemistryVol. 14(6)
Hanyang University (KR), Anyang University (KR)
Openalex Percentile: Top 17%
Surfactants and Colloidal Systems
1.87
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Mixed Surfactant Nano‐Assemblies for Allylic Alcohol Etherification in Aqueous Medium — Pil Seok Chae, Waqar Ahmed, et al. · Asian Journal of Organic Chemistry (2025) | TGRS Research Map | TGRS