Trityl Chloride as a Novel and Efficient Organic Catalyst For Room Temperature Preparation of Bis(indolyl)methanes under Solvent-Free Conditions in Neutral Media

A. Khalafi-Nezhad; A. Parhami; A. Zare; A. R. Moosavi Zare; A. Hasaninejad; F. Panahi

doi:10.1055/s-2008-1032159

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Synthesis 2008(4): 617-621
DOI: 10.1055/s-2008-1032159

PAPER

Trityl Chloride as a Novel and Efficient Organic Catalyst For Room Temperature Preparation of Bis(indolyl)methanes under Solvent-Free Conditions in Neutral Media

A. Khalafi-Nezhad*^a, A. Parhami^a, A. Zare^b, A. R. Moosavi Zare^a, A. Hasaninejad^c, F. Panahi^a
^a Department of Chemistry, College of Sciences, Shiraz University, Shiraz 71454, Iran
Fax: +98(711)2280926; e-Mail: khalafi@chem.susc.ac.ir;
^b Department of Chemistry, Payame Noor University of Bushehr, Bushehr 1698, Iran
^c Department of Chemistry, Faculty of Sciences, Persian Gulf University, Bushehr 75169, Iran

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Publication History

Received 22 October 2007
Publication Date:
31 January 2008 (online)

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Abstract

A simple, clean, and highly efficient solvent-free procedure for the preparation of bis(1H-indol-3-yl)methanes is described from the reaction of carbonyl compounds (aldehydes and ketones) with 1H-indole in the presence of trityl chloride as a catalyst. The reaction proceeds rapidly in high yields at room temperature in a neutral medium. A proposed mechanism is suggested based upon former reactions and calculated results.

Key words

trityl chloride - bis(indolyl)methanes - carbonyl compounds - indole - solvent-free

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In order to make the procedure safer and greener (for the reactions that require higher temperatures than r.t.) it is also possible to transfer the crude reaction into a small round-bottomed flask (equipped with a reflux condenser) and use an oil bath instead of an oven.