Issue 10, 2012
From the journal:

Green Chemistry

CeIII-promoted oxidation. Efficient aerobic one-pot eco-friendly synthesis of oxidized bis(indol-3-yl)methanes and cyclic tetra(indolyl)dimethanes†

Claudio C. Silveira,*a   Samuel R. Mendes,b   Marcos A. Villetti,a   Davi F. Backa  and  Teodoro S. Kaufman*c  

* Corresponding authors

a Departamento de Química, Universidade Federal de Santa Maria, Santa Maria, RS, Brazil
E-mail: silveira@quimica.ufsm.br
Tel: +55-55-3220-8754

b Departamento de Química, Universidade do Estado de Santa Catarina, Joinville, SC, Brazil
E-mail: samuel.mendes@udesc.br

c Instituto de Química Rosario (CONICET-UNR), Suipacha 531, Rosario, SF, Argentina
E-mail: kaufman@iquir-conicet.gov.ar
Tel: +54-341-4370477

Abstract

Indoles and benzaldehyde derivatives undergo an efficient one-pot smooth condensation and a further atmospheric-pressure aerobic dehydrogenation with CeCl3 in i-PrOH, to afford the corresponding oxidized bis(indol-3-yl)methanes. Use of 2,2′-bisindole as the heterocyclic precursor provides cyclic tetra(indolyl)dimethane derivatives, which further undergo partial oxidation to the related calix-shaped macrocycles, carrying an all cis 1,3,7-cyclodecatriene core and supporting a 2,2′-biindolylidene moiety. The syntheses of these high value-added compounds is operationally simple and can be performed at room temperature under mild, neutral and environmentally friendly conditions.

Graphical abstract: CeIII-promoted oxidation. Efficient aerobic one-pot eco-friendly synthesis of oxidized bis(indol-3-yl)methanes and cyclic tetra(indolyl)dimethanes

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Article information

DOI
https://doi.org/10.1039/C2GC36131K
Article type
Paper
Submitted
15 Jun 2012
Accepted
02 Aug 2012
First published
03 Aug 2012

Green Chem., 2012,14, 2912-2921

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CeIII-promoted oxidation. Efficient aerobic one-pot eco-friendly synthesis of oxidized bis(indol-3-yl)methanes and cyclic tetra(indolyl)dimethanes

C. C. Silveira, S. R. Mendes, M. A. Villetti, D. F. Back and T. S. Kaufman, Green Chem., 2012, 14, 2912 DOI: 10.1039/C2GC36131K

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