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Issue 18, 2015
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Palladium(II)-catalyzed intramolecular carboxypalladation–olefin insertion cascade: direct access to indeno[1,2-b]furan-2-ones

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Abstract

A catalytic, atom-economical, domino 5-endo-dig cyclization–intramolecular olefin insertion sequence was developed under mild conditions. Aryl alkynoic acids bearing a tethered enone partner afforded the indeno[1,2-b]furan-2-ones, the core skeleton present in a number of biologically significant molecules including the natural product solanacol, under ligand-free, palladium-catalyzed reaction conditions in high yields. The competitive β-hydride elimination in the final step leading to the conjugated analogs was avoided by the addition of lithium bromide. A plausible mechanism for this domino sequence is proposed involving intramolecular carboxypalladation and olefin insertion steps.

Graphical abstract: Palladium(ii)-catalyzed intramolecular carboxypalladation–olefin insertion cascade: direct access to indeno[1,2-b]furan-2-ones

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Publication details

The article was received on 07 Mar 2015, accepted on 25 Mar 2015 and first published on 26 Mar 2015


Article type: Paper
DOI: 10.1039/C5OB00458F
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Citation: Org. Biomol. Chem., 2015,13, 5175-5181
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    Palladium(II)-catalyzed intramolecular carboxypalladation–olefin insertion cascade: direct access to indeno[1,2-b]furan-2-ones

    P. Vinoth, T. Vivekanand, P. A. Suryavanshi, J. C. Menéndez, H. Sasai and V. Sridharan, Org. Biomol. Chem., 2015, 13, 5175
    DOI: 10.1039/C5OB00458F

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