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通过酸/碘化物协同催化实现羧酸与O-H亲核试剂的高效酯化反应。

Highly efficient esterification of carboxylic acids with O-H nucleophiles through acid/iodide cooperative catalysis.

作者信息

Zuo Dongxu, Xiao Xiong, Ma Xinyue, Nie Peng, Liu Long, Chen Tieqiao

机构信息

Key Laboratory of Ministry of Education for Advanced Materials in Tropical Island Resources, Hainan Provincial Key Lab of Fine Chem, Hainan Provincial Fine Chemical Engineering Research Center, Hainan University, Haikou, 570228, China.

Guizhou Institute for Food and Drug Control, 84 Shibei Road, Yunyan District, Guiyang City, Guizhou Province, 550000, China.

出版信息

Org Biomol Chem. 2024 Jul 31;22(30):6181-6188. doi: 10.1039/d4ob00910j.

DOI:10.1039/d4ob00910j
PMID:39016558
Abstract

The esterification of carboxylic acids is an important reaction for preparing esters which find wide applications in various research fields. In this manuscript, we report an acid/iodide cooperative catalytic method which enables highly efficient esterification of carboxylic acids with a wide range of equivalent O-H nucleophiles including both alcohols and weak nucleophilic phenols. Under the reaction conditions, both aromatic and aliphatic carboxylic acids including those bearing functional groups work well, furnishing the corresponding esters in good to high yields. Moreover, this reaction is scalable and applicable to the modification of bioactive molecules. These results demonstrate the synthetic value of this new reaction in organic synthesis.

摘要

羧酸的酯化反应是制备酯类的重要反应,酯类在各个研究领域都有广泛应用。在本论文中,我们报道了一种酸/碘化物协同催化方法,该方法能够使羧酸与多种当量的O-H亲核试剂(包括醇类和弱亲核性的酚类)进行高效酯化反应。在该反应条件下,包括带有官能团的芳香族和脂肪族羧酸都能顺利反应,以良好至高收率得到相应的酯。此外,该反应具有可扩展性,适用于生物活性分子的修饰。这些结果证明了这种新反应在有机合成中的合成价值。

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