Facile and General Aryl Ester Synthesis via Transesterification of NHPI Ester with Phenols

Abstract The widespread presence of aryl esters in natural products, pharmaceuticals, fragrances, functional materials, and fine chemicals, coupled with increasing demands in chemistry, chemical industry, and other scientific fields, necessitates the development of green and efficient synthetic methods for their structurally and functionally diverse synthesis. Yet, its reporting remains scarce, despite the fact that esterification reaction has been advancing for nearly two centuries. Herein, we present a facile, specific, and general aryl ester synthesis from phenols and N ‐hydroxyphthalimide (NHPI) esters (as acylation reagents) in the presence of only an inorganic base. This facile protocol enables the synthesis of a broad range of aryl esters, as well as analogues of gemfibrozil, estrogen drugs, and aryl ester liquid crystals, with high yields and remarkable tolerance of reactive functional groups. Thus, it presents an ideal and reliable alternative for aryl ester synthesis.

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Publication Details

Journal
Asian Journal of Organic Chemistry
Published
2025-04-23
DOI
https://doi.org/10.1002/ajoc.202500329
Primary Topic
Chemical Synthesis and Reactions
Type
article
Field-Weighted Citation Impact
0.00

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article

Facile and General Aryl Ester Synthesis via Transesterification of NHPI Ester with Phenols

Yongbo Zhou, Xinyang Gan, Jianyu Dong, Jie Huo et al.
Asian Journal of Organic Chemistry
Chemical Synthesis and Reactions
article

Facile and General Aryl Ester Synthesis via Transesterification of NHPI Ester with Phenols

Yongbo Zhou, Xinyang Gan, Jianyu Dong, Jie Huo, Shuang Yin, Feng Liu, Qiong Su
article en

Abstract

Abstract The widespread presence of aryl esters in natural products, pharmaceuticals, fragrances, functional materials, and fine chemicals, coupled with increasing demands in chemistry, chemical industry, and other scientific fields, necessitates the development of green and efficient synthetic methods for their structurally and functionally diverse synthesis. Yet, its reporting remains scarce, despite the fact that esterification reaction has been advancing for nearly two centuries. Herein, we present a facile, specific, and general aryl ester synthesis from phenols and N ‐hydroxyphthalimide (NHPI) esters (as acylation reagents) in the presence of only an inorganic base. This facile protocol enables the synthesis of a broad range of aryl esters, as well as analogues of gemfibrozil, estrogen drugs, and aryl ester liquid crystals, with high yields and remarkable tolerance of reactive functional groups. Thus, it presents an ideal and reliable alternative for aryl ester synthesis.

Asian Journal of Organic ChemistryVol. 14(7)
Hunan University (CN), Ministry of Education (SA), State Key Laboratory of Chemobiosensing and Chemometrics (CN), Hunan First Normal University (CN)
National Key Research and Development Program of China
Openalex Percentile: Top 93%
Chemical Synthesis and Reactions
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