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Synlett 2020; 31(18): 1775-1788
DOI: 10.1055/s-0040-1707152
DOI: 10.1055/s-0040-1707152
account
Dearomatization Reactions of Indoles to Access 3D Indoline Structures
The research leading to the results summarized in this account has received funding from the ANR (ANR-17-CE07-0050 “ArDCo” and ANR-12-JS07-0002 “CouPhIn), the European Union's Seventh Framework Programme FP7/2007-2013/ under REA grant agreement n° 623422 (“ElectrIndole”), Labex CHARMMMAT (ANR-11-LABX-0039), the China Scholarship Council, the “Ministère de l’Enseignement Supérieur, de la Recherche et de l’Innovation, the Université Paris-Sud and the CNRS.
Further Information
Publication History
Received: 26 April 2020
Accepted after revision: 23 May 2020
Publication Date:
24 June 2020 (online)
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
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Seminal contribution:
For a review, see:
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For the synthesis of 2-phosphonoindoles, see:
Selected examples:
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For the synthesis of related hydroxypyranoindoline derivatives via dearomatization, see:
For the synthesis of related 3,3-spiro-3-amino-2-hydroxyindoline derivatives via dearomatization, see:
For selective nonelectrochemical dearomative diazidations of indoles, see: