铜催化2-羰基吲哚的1,4-羧酸酯脱芳重排†

Organic chemistry frontiers : an international journal of organic chemistry Pub Date : 2023-01-01 DOI:10.1039/d2qo01647h

Yan Zhu , Ying Shao , Shengbiao Tang , Jiangtao Sun

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引用次数: 0

摘要

在铜催化剂的存在下，2-羰基吲哚与芳基重氮乙酸酯进行了一种新的脱芳1，4-重排反应，该反应可能通过串联形成两性离子中间体进行，分子内环化和开环反应得到最终的重排产物，该重排产物含有一个具有两个新形成的C–C键的全碳四元中心。在这个序列中，吲哚的芳香性被破坏，与1,4-羧酸盐重排有关。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

Copper-catalyzed dearomative 1,4-carboxylate rearrangement of 2-carbonateindoles†

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Copper-catalyzed dearomative 1,4-carboxylate rearrangement of 2-carbonateindoles†

A novel dearomative 1,4-rearrangement reaction of 2-carbonateindoles with aryl diazoacetates has been developed in the presence of a copper catalyst, which might proceed through a tandem formation of a zwitterionic intermediate, intramolecular cyclization and ring-opening reaction to give the final rearrangement products containing an all-carbon quaternary center with two newly formed C–C bonds. In this sequence, the disruption of the aromaticity of indole has been realized, associated with 1,4-carboxylate rearrangements.

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来源期刊

Organic chemistry frontiers : an international journal of organic chemistry

CiteScore

7.80

自引率

0.00%

发文量