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Issue 8, 2011
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Synthesis of benzo- and naphtho-fused bicyclo[n.3.1]alkane frameworks with a bridgehead nitrogen function by palladium-catalyzed intramolecular α′-arylation of α-nitroketones

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Abstract

The C-alkylation of cyclic α-nitroketones with α-halobenzyl halides in the presence of DBU followed by a Pd-catalyzed intramolecular C-arylation afforded benzo-and naphtho-fused bicyclo[n.3.1]alkane derivatives (n = 3, 4, 5) in excellent overall yields for the two-step sequence. In some of the reactions starting from α-nitrocyclooctanone, the major products were fused indane derivatives arising from an intramolecular attack of an intermediate Pd species onto the carbonyl group, followed by elimination.

Graphical abstract: Synthesis of benzo- and naphtho-fused bicyclo[n.3.1]alkane frameworks with a bridgehead nitrogen function by palladium-catalyzed intramolecular α′-arylation of α-nitroketones

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Publication details

The article was received on 01 Aug 2010, accepted on 06 Jan 2011 and first published on 07 Jan 2011


Article type: Paper
DOI: 10.1039/C0OB00526F
Citation: Org. Biomol. Chem., 2011,9, 2722-2730
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    Synthesis of benzo- and naphtho-fused bicyclo[n.3.1]alkane frameworks with a bridgehead nitrogen function by palladium-catalyzed intramolecular α′-arylation of α-nitroketones

    G. Giorgi, S. Maiti, P. López-Alvarado and J. C. Menéndez, Org. Biomol. Chem., 2011, 9, 2722
    DOI: 10.1039/C0OB00526F

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