Issue 1, 2023
From the journal:

Organic Chemistry Frontiers

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

Yan Zhu,a   Ying Shao,a   Shengbiao Tang ORCID logo a  and  Jiangtao Sun ORCID logo *a  

* Corresponding authors

a Jiangsu Key Laboratory of Advanced Catalytic Materials & Technology, School of Petrochemical Engineering, Changzhou University, Changzhou 213164, China
E-mail: jtsun@cczu.edu.cn

Abstract

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.

Graphical abstract: Copper-catalyzed dearomative 1,4-carboxylate rearrangement of 2-carbonateindoles

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Article information

DOI
https://doi.org/10.1039/D2QO01647H
Article type
Research Article
Submitted
18 Oct 2022
Accepted
11 Nov 2022
First published
14 Nov 2022

Org. Chem. Front., 2023,10, 99-103

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

Y. Zhu, Y. Shao, S. Tang and J. Sun, Org. Chem. Front., 2023, 10, 99 DOI: 10.1039/D2QO01647H

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