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Issue 1, 2013
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Diversity oriented synthesis of indole-based peri-annulated compounds via allylic alkylation reactions

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Abstract

Diverse indole-based peri-annulated compounds were synthesized via transition-metal-catalyzed allylic alkylation reaction. With palladium catalyst, indole-based nine-membered ring products were obtained in 40–70% yields. When iridium catalyst was used, highly enantioenriched seven-membered ring products were obtained in 40–78% yields and 91–97% ee. Meanwhile, when 3-substituted indole substrates were employed with a palladium catalyst, asymmetric allylic dearomatization of indoles occurred with products obtained in 48–78% yields and 35–78% ee with a chiral ferrocene-based Phox ligand. Interestingly, with an iridium catalyst, Friedel–Crafts type allylic alkylation reaction proceeded at the C5 position of indole, affording the products with 40–60% yields and 56–97% ee.

Graphical abstract: Diversity oriented synthesis of indole-based peri-annulated compounds via allylic alkylation reactions

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Publication details

The article was received on 26 Jul 2012, accepted on 23 Aug 2012 and first published on 24 Aug 2012


Article type: Edge Article
DOI: 10.1039/C2SC21085A
Citation: Chem. Sci., 2013,4, 97-102
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    Diversity oriented synthesis of indole-based peri-annulated compounds via allylic alkylation reactions

    Q. Xu, L. Dai and S. You, Chem. Sci., 2013, 4, 97
    DOI: 10.1039/C2SC21085A

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