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Issue 40, 2017
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Transition-metal-catalyzed divergent functionalization of [60]fullerene with propargylic esters

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Abstract

We have demonstrated that transition-metal-catalyzed divergent reactions between [60]fullerene (C60) and propargylic esters allow easy access to formal [2 + 2] and [4 + 2] cycloadducts in reasonable yields, and that the production ratios depend on the metal catalyst used. The molecular structures of the cycloadducts were characterized by means of spectroscopic analyses and theoretical calculations. A plausible reaction mechanism is proposed that shows that two competing routes are likely to be involved after the initial transition-metal-activated cyclization of the carbonyl group and the C–C triple bond in the 6-endo-dig mode. Further rearrangement into allenol esters followed by formal [2 + 2] cycloaddition with C60 gives the [2 + 2] cycloadducts, whereas rearrangement into 1,3-dienyl esters followed by [4 + 2] cycloaddition with C60 gives the [4 + 2] cycloadducts.

Graphical abstract: Transition-metal-catalyzed divergent functionalization of [60]fullerene with propargylic esters

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Publication details

The article was received on 30 Aug 2017, accepted on 15 Sep 2017 and first published on 15 Sep 2017


Article type: Communication
DOI: 10.1039/C7OB02168B
Citation: Org. Biomol. Chem., 2017,15, 8499-8503
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    Transition-metal-catalyzed divergent functionalization of [60]fullerene with propargylic esters

    M. Yamada, R. Ochi, Y. Yamamoto, S. Okada and Y. Maeda, Org. Biomol. Chem., 2017, 15, 8499
    DOI: 10.1039/C7OB02168B

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