Issue 19, 2016

Reactivity of alkynylindole-2-carboxamides in [Pd]-catalysed C–H activation and phase transfer catalysis: formation of pyrrolo-diindolones vs. β-carbolinones

Abstract

The divergent behaviour of 3-alkynylindole-2-carboxamides, under palladium catalysed conditions and phase-transfer catalytic conditions, is described. Thus, palladium catalysed intramolecular C–N and C–C bond formation in a single step by C–H activation involving 3-alkynylindole-2-carboxamides and leading to pyrrolodiindolones in high yields is developed. In contrast, using the same precursors, a high yielding regio- and chemo-selective route for 3-substituted β-carbolinones by phase-transfer catalysis is established via intramolecular C–N bond formation. The structures of key products are confirmed by X-ray crystallography.

Graphical abstract: Reactivity of alkynylindole-2-carboxamides in [Pd]-catalysed C–H activation and phase transfer catalysis: formation of pyrrolo-diindolones vs. β-carbolinones

Supplementary files

Article information

Article type
Paper
Submitted
17 Mar 2016
Accepted
08 Apr 2016
First published
11 Apr 2016

Org. Biomol. Chem., 2016,14, 4519-4533

Reactivity of alkynylindole-2-carboxamides in [Pd]-catalysed C–H activation and phase transfer catalysis: formation of pyrrolo-diindolones vs. β-carbolinones

R. N. P. Tulichala and K. C. K. Swamy, Org. Biomol. Chem., 2016, 14, 4519 DOI: 10.1039/C6OB00583G

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