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Iron(II) Triflate as a Catalyst for the Synthesis of Indoles by Intramolecular C-H Amination

Julien Bonnamour and Carsten Bolm*

*Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, D-52056 Aachen, Germany, Email: carsten.bolmoc.rwth-aachen.de

J. Bonnamour, C. Bolm, Org. Lett., 2011, 13, 2012-2014.

DOI: 10.1021/ol2004066


Abstract

A practical iron-catalyzed intramolecular C-H amination reaction with commercially available iron(II) triflate as catalyst can be used for the synthesis of indole derivatives.


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General procedure for metal-catalyzed cyclizations of aryl azidoacrylates

A sealable tube equipped with a magnetic stir bar was charged with the aryl azidoacrylates (100 mg, 1.0 equiv) and Fe(OTf)2 (10 mol %). The aperture of the tube was then covered with a rubber septum, and an argon atmosphere was established. THF (1 mL) as added by syringe. The septum was then replaced by a teflon-coated screw cap, and the reaction vessel was placed in an oil bath (80 C). After stirring at this temperature for 24 h, the mixture was cooled to room temperature and diluted with dichloromethane. The resulting solution was directly filtered through a pad of celite, washed with water, extracted with dichloromethane and concentrated to yield the product, which was purified by silica gel chromatography to yield the corresponding indole as a white solid. The identity and purity of the product was confirmed by 1H and 13C NMR spectroscopic analysis.


Key Words

Indoles


ID: J54-Y2011-1090