Reactivity of alkynylindole-2-carboxamides in [Pd]-catalysed C–H activation and phase transfer catalysis: formation of pyrrolo-diindolones vs. β-carbolinones?
Organic & Biomolecular Chemistry Pub Date: 2016-04-11 DOI: 10.1039/C6OB00583G
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](http://scimg.chem960.com/usr/1/C6OB00583G.jpg)
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Journal Name：Organic & Biomolecular Chemistry
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CAS no.: 89640-58-4
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