Issue 21, 2015
From the journal:

Chemical Communications

Efficient direct 2,2,2-trifluoroethylation of indoles via C–H functionalization†‡

Gergely L. Tolnai,§a   Anna Székely,§a   Zita Makó,a   Tamás Gáti,b   János Daru,c   Tamás Bihari,c   András Stirling*c  and  Zoltán Novák*a  

* Corresponding authors

a MTA-ELTE “Lendület” Catalysis and Organic Synthesis Research Group, Institute of Chemistry, Eötvös University, Faculty of Science, Pázmány Péter stny. 1/A, Budapest, Hungary
E-mail: novakz@elte.hu
Web: http://zng.elte.hu

b Servier Research Institute of Medicinal Chemistry, Záhony utca 7, H-1031 Budapest, Hungary

c Research Centre for Natural Sciences of the Hungarian Academy of Sciences, Department of Theoretical Chemistry, Magyar Tudósok körútja 2, 1117 Budapest, Hungary
E-mail: stirling.andras@ttk.mta.hu

Abstract

A novel highly C3 selective metal free trifluoroethylation of indoles using 2,2,2-trifuoroethyl(mesityl)-iodonium triflate was developed. The methodology enables the introduction of a trifluoroethyl group in a fast and efficient reaction under mild conditions with high functional group tolerance. Beyond the synthetic developments, quantum chemical calculations provide a deeper understanding of the transformation.

Graphical abstract: Efficient direct 2,2,2-trifluoroethylation of indoles via C–H functionalization

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Article information

DOI
https://doi.org/10.1039/C5CC00519A
Article type
Communication
Submitted
19 Jan 2015
Accepted
05 Feb 2015
First published
06 Feb 2015
This article is Open Access
Creative Commons BY license

Chem. Commun., 2015,51, 4488-4491

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Efficient direct 2,2,2-trifluoroethylation of indoles via C–H functionalization

G. L. Tolnai, A. Székely, Z. Makó, T. Gáti, J. Daru, T. Bihari, A. Stirling and Z. Novák, Chem. Commun., 2015, 51, 4488 DOI: 10.1039/C5CC00519A

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