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十聚钨酸盐光催化吲哚的去芳构化氢酰化反应:2-酰基吲哚啉的直接合成

Decatungstate-Photocatalyzed Dearomative Hydroacylation of Indoles: Direct Synthesis of 2-Acylindolines.

作者信息

Varlet Thomas, Bouchet Damien, Van Elslande Elsa, Masson Géraldine

机构信息

Institut de Chimie des Substances Naturelles (ICSN) CNRS, University Paris-Saclay, 1 Avenue de la Terrasse, 91198, Gif-sur-Yvette Cedex, France.

HitCat, Seqens-CNRS joint laboratory, Seqens'Lab, 8 Rue de Rouen, 78440, Porcheville, France.

出版信息

Chemistry. 2022 Oct 7;28(56):e202201707. doi: 10.1002/chem.202201707. Epub 2022 Aug 17.

Abstract

We report herein a convenient and scalable dearomative hydroacylation reaction of indoles. Employing readily available aldehydes as the acyl source and TBADT as an inexpensive direct HAT photocatalyst, a variety of indoles derivatives were converted into synthetically interesting 2-acylindolines in good to excellent yields as well as great diastereoselectivity under mild conditions. An asymmetric version of the reaction was successfully developed and an experimental mechanistic investigation was carried out in order to gain further insights on the assumed reaction pathway.

摘要

我们在此报告一种便捷且可扩展的吲哚去芳构化氢酰化反应。使用易于获得的醛作为酰基源,四丁基铵二硫代苯甲酸酯(TBADT)作为廉价的直接氢原子转移(HAT)光催化剂,在温和条件下,多种吲哚衍生物以良好至优异的产率以及出色的非对映选择性转化为具有合成意义的2-酰基吲哚啉。该反应的不对称版本得以成功开发,并进行了实验机理研究,以便对假定的反应途径有更深入的了解。

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