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使用铌酸和负载钯碳双重催化的环己酮对吲哚进行芳基化反应。

Arylation of indoles using cyclohexanones dually-catalyzed by niobic acid and palladium-on-carbons.

机构信息

Laboratory of Organic Chemistry, Gifu Pharmaceutical University, 1-25-4 Daigakunishi, Gifu 501-1196, Japan.

出版信息

Org Biomol Chem. 2020 May 28;18(20):3898-3902. doi: 10.1039/d0ob00702a. Epub 2020 May 12.

Abstract

3-Arylindoles were easily constructed from indoles and cyclohexanone derivatives using a combination of catalytic niobic acid-on-carbon (NbO/C) and palladium-on-carbon (Pd/C) under heating conditions without any oxidants. The Lewis acidic NbO/C promoted the nucleophilic addition of indoles to the cyclohexanones, and the subsequent dehydration and Pd/C-catalyzed dehydrogenation produced the 3-arylindoles. The additive 2,3-dimethyl-1,3-butadiene worked as a hydrogen acceptor to facilitate the dehydrogenation step.

摘要

3-芳基吲哚类化合物可通过在无氧化剂条件下,使用负载型铌酸(NbO/C)和负载型钯(Pd/C)的协同催化作用,由吲哚和环己酮衍生物加热制备得到。Lewis 酸性的 NbO/C 促进了吲哚对环己酮的亲核加成,随后的脱水和 Pd/C 催化脱氢生成了 3-芳基吲哚类化合物。添加剂 2,3-二甲基-1,3-丁二烯作为氢受体促进了脱氢步骤。

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