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三氟甲氧基邻苯二甲酰亚胺:一种用于亲核三氟甲氧基化的稳定试剂。

-Trifluoromethoxyphthalimide: A Shelf-Stable Reagent for Nucleophilic Trifluoromethoxylation.

机构信息

Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Science, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032, China.

出版信息

J Org Chem. 2023 Apr 7;88(7):4434-4441. doi: 10.1021/acs.joc.2c03031. Epub 2023 Mar 15.

Abstract

Due to the unique properties of the OCF group, trifluoromethyl ether compounds play an important role in pharmaceuticals and agrochemicals. Recently, considerable attention has been focused on the development of practical and convenient reagents for the direct incorporation of the OCF group into organic compounds. Herein, we reported a new trifluoromethoxylating reagent -trifluoromethoxyphthalimide (Phth-OCF). The reagent was a stable solid and released an OCF anion under mild reaction conditions. We demonstrated the application of Phth-OCF for the nucleophilic trifluoromethoxylation of various alkyl electrophiles.

摘要

由于 OCF 基团的独特性质,三氟甲醚类化合物在药物和农用化学品中起着重要作用。最近,人们对开发实用、方便的试剂以将 OCF 基团直接引入有机化合物的研究产生了浓厚的兴趣。在此,我们报道了一种新的三氟甲氧基化试剂——三氟甲氧基邻苯二甲酰亚胺(Phth-OCF)。该试剂为稳定的固体,在温和的反应条件下释放出 OCF 阴离子。我们展示了 Phth-OCF 在各种烷基亲电试剂的亲核三氟甲氧基化反应中的应用。

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