An unprecedented reactivity of aryl azides toward alkynes is presented herein. The reaction performed well in the presence of 2 mol % of ruthenium porphyrin catalysts and afforded substituted indoles instead of triazoles. The procedure is particularly appealing for the synthesis of C3-functionalized indoles which bear EWG on the fragment coming from the azide. The method allowed the synthesis of 15 derivatives with yields up to 95%, high regioselectivity, and without requiring the time-consuming prefunctionalization of reagents and the addition of oxidants and/or additives.

Indoles rather than triazoles from the ruthenium porphyrin-catalyzed reaction of alkynes with aryl azides / P. Zardi, A. Savoldelli, D.M. Carminati, A. Caselli, F. Ragaini, E. Gallo. - In: ACS CATALYSIS. - ISSN 2155-5435. - 4:11(2014 Nov 07), pp. 3820-3823.

Indoles rather than triazoles from the ruthenium porphyrin-catalyzed reaction of alkynes with aryl azides

P. Zardi
Primo
;
D.M. Carminati;A. Caselli;F. Ragaini
Penultimo
;
E. Gallo
2014

Abstract

An unprecedented reactivity of aryl azides toward alkynes is presented herein. The reaction performed well in the presence of 2 mol % of ruthenium porphyrin catalysts and afforded substituted indoles instead of triazoles. The procedure is particularly appealing for the synthesis of C3-functionalized indoles which bear EWG on the fragment coming from the azide. The method allowed the synthesis of 15 derivatives with yields up to 95%, high regioselectivity, and without requiring the time-consuming prefunctionalization of reagents and the addition of oxidants and/or additives.
alkyne; azide; indole; porphyrin; ruthenium; catalysis
Settore CHIM/03 - Chimica Generale e Inorganica
Article (author)
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2434/246749
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