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TBAF catalyzed one-pot synthesis of allenyl-indoles

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Abstract

The site selective synthesis of functionalized indoles is presented under environmentally convenient tetrabutylammonium fluoride catalysis. The metal-free approach exploits the combined efficiency of Bu4N+ and F ions in performing a cascade sequence involving intramolecular hydroamination of the C–C triple bond, cleavage of silyl-protecting groups and site-selective sigmatropic aza-Cope-type [3,3]-rearrangement. A range of C(3)-allenyl-(1H)-indoles (2) is obtained in an efficient manner (yield up to 93%) providing a valuable synthetic alternative to noble metal-based protocols.

Graphical abstract: TBAF catalyzed one-pot synthesis of allenyl-indoles

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Publication details

The article was received on 25 May 2017, accepted on 13 Jun 2017 and first published on 13 Jun 2017


Article type: Research Article
DOI: 10.1039/C7QO00414A
Citation: Org. Chem. Front., 2017, Advance Article
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    TBAF catalyzed one-pot synthesis of allenyl-indoles

    A. De Nisi, S. Sierra, M. Ferrara, M. Monari and M. Bandini, Org. Chem. Front., 2017, Advance Article , DOI: 10.1039/C7QO00414A

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