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铱(I)催化的吲哚 C2 位与烯烃的 C-H 键烷基化反应:线性或支链 2-烷基吲哚的选择性合成。

Ir(I)-catalyzed C-H bond alkylation of C2-position of indole with alkenes: selective synthesis of linear or branched 2-alkylindoles.

机构信息

Department of Chemistry and Biochemistry, School of Advanced Science and Engineering, Waseda University, Shinjuku, Tokyo, 169-8555, Japan.

出版信息

J Am Chem Soc. 2012 Oct 24;134(42):17474-7. doi: 10.1021/ja308742x. Epub 2012 Oct 12.

Abstract

A cationic iridium-catalyzed C2-alkylation of N-substituted indole derivatives with various alkenes has been developed, which selectively gives linear or branched 2-alkylindoles in high to excellent selectivity. This protocol relies on the use of the carbonyl group on the nitrogen atom of indole as a directing group: a linear product was predominant when an acetyl group was used as a directing group, and a branched product was predominant with a benzoyl group.

摘要

发展了一种新型的铱催化的 N-取代吲哚衍生物与各种烯烃的 C2-烷基化反应,该反应具有高度的区域选择性和优异的立体选择性,可得到线性或支链的 2-烷基吲哚产物。该反应的关键是利用吲哚氮原子上的羰基作为导向基团:当使用乙酰基作为导向基团时,主要生成线性产物;而当使用苯甲酰基作为导向基团时,则主要生成支链产物。

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