Dearomatization Reactions of Indoles to Access 3D Indoline Structures

Hussein Abou-Hamdan; Cyrille Kouklovsky; Guillaume Vincent

doi:10.1055/s-0040-1707152

Synlett, Table of Contents

Synlett 2020; 31(18): 1775-1788
DOI: 10.1055/s-0040-1707152

account

Dearomatization Reactions of Indoles to Access 3D Indoline Structures

Hussein Abou-Hamdan

,

Cyrille Kouklovsky

,

Guillaume Vincent ∗

Abstract

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Abstract

This Account summarizes our involvement in the development of dearomatization reactions of indoles that has for origin a total synthesis problematic. We present the effort from our group to obtain 3D-indolines scaffold from the umpolung of N-acyl indoles via activation with FeCl₃ to the oxidative spirocyclizations of N-EWG indoles and via the use of electrochemistry.

1 Introduction

2 Activation of N-Acyl Indoles with FeCl₃

2.1 Hydroarylation of N-Acyl Indoles

2.2 Difunctionalization of N-Acyl Indoles

3 Radical-Mediated Dearomatization of Indoles for the Synthesis of Spirocyclic Indolines

4 Electrochemical Dearomatization of Indoles

4.1 Direct Electrochemical Oxidation of Indoles

4.2 Indirect Electrochemical Oxidation of Indoles

5 Conclusion

Key words

indole - dearomatization - indolines - FeCl₃ - radical chemistry - electrochemistry

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