Synthesis 2008(4): 617-621  
DOI: 10.1055/s-2008-1032159
PAPER
© Georg Thieme Verlag Stuttgart · New York

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. Parhamia, A. Zareb, A. R. Moosavi Zarea, A. Hasaninejadc, F. Panahia
a Department of Chemistry, College of Sciences, Shiraz University, Shiraz 71454, Iran
Fax: +98(711)2280926; e-Mail: [email protected];
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
Further Information

Publication History

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

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.

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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.