将炔酸的三官能化、烯原位 C-H 官能化和胺化结合起来：非对称 2,3-二芳基取代吲哚的制备方法

IF 4.9 1区化学 Q1 CHEMISTRY, ORGANIC Organic Letters Pub Date : 2024-10-30 DOI:10.1021/acs.orglett.4c03446

Narges Mohammadi, Farid Mohaghegh, Mehran Ghasemi, Farnaz Jafarpour

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引用次数: 0

摘要

在此，我们报告了一种同时构建两个 C-C 键和两个 C-N 键的统一方法，该方法结合了炔酸三官能化、正交 C-H 官能化和胺化级联反应。在有序过程中，区域选择性炔插入反应比脱羧过程更有利。炔酸中羧基的存在确保了羰基钯化过程的高区域选择性，为合成具有优异区域选择性的非对称 2,3 二芳基取代吲哚支架的新方法铺平了道路。实验证明该方法适用于克级合成。

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Combining Trifunctionalization of Alkynoic Acids, Arene ortho C–H Functionalization and Amination: An Approach to Unsymmetrical 2,3-Diaryl Substituted Indoles

Here we report a simultaneous construction of two C–C and two C–N bonds in a unified procedure that incorporates alkynoic acid trifunctionalization, ortho C–H functionalization, and amination cascade. In an ordered process, the regioselective alkyne insertion reaction is favored over the decarboxylation process. The presence of the carboxyl group in alkynoic acid ensures the high regioselectivity in the carbopalladation process, paving the way for a novel method to synthesize unsymmetrically 2,3-diaryl substituted indole scaffolds with excellent regioselectivity. The protocol is demonstrated to be suitable for gram-scale synthesis.

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来源期刊

Organic Letters 化学-有机化学

CiteScore

9.30

自引率

11.50%

发文量

1607

审稿时长

1.5 months

期刊介绍： Organic Letters invites original reports of fundamental research in all branches of the theory and practice of organic, physical organic, organometallic,medicinal, and bioorganic chemistry. Organic Letters provides rapid disclosure of the key elements of significant studies that are of interest to a large portion of the organic community. In selecting manuscripts for publication, the Editors place emphasis on the originality, quality and wide interest of the work. Authors should provide enough background information to place the new disclosure in context and to justify the rapid publication format. Back-to-back Letters will be considered. Full details should be reserved for an Article, which should appear in due course.