Indoles Rather than Triazoles from the Ruthenium Porphyrin-Catalyzed Reaction of Alkynes with Aryl Azides
2014; American Chemical Society; Volume: 4; Issue: 11 Linguagem: Inglês
10.1021/cs5012712
ISSN2155-5435
AutoresPaolo Zardi, Andrea Savoldelli, Daniela Maria Carminati, Alessandro Caselli, Fabio Ragaini, Emma Gallo,
Tópico(s)Synthesis and Catalytic Reactions
ResumoAn 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.
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