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Issue 46, 2017
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Hemin-catalyzed sulfonium ylide formation and subsequently reactant-controlled chemoselective rearrangements

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Abstract

Hemin-catalyzed competing routes of [1,2]-Stevens and Sommelet–Hauser rearrangements of benzyl sulfonium ylides through an iron porphyrin carbenoid were established. These rearrangements can be controlled by the electronic property of the substituents on the benzyl group together with solvent effects. Electron-donating or weak electron-withdrawing groups lead to the [1,2]-Stevens rearrangement, whereas strong electron-withdrawing groups at the para-position favor the latter pathway under aqueous conditions.

Graphical abstract: Hemin-catalyzed sulfonium ylide formation and subsequently reactant-controlled chemoselective rearrangements

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Publication details

The article was received on 31 Mar 2017, accepted on 05 May 2017 and first published on 10 May 2017


Article type: Communication
DOI: 10.1039/C7CC02484C
Citation: Chem. Commun., 2017,53, 6219-6222
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    Hemin-catalyzed sulfonium ylide formation and subsequently reactant-controlled chemoselective rearrangements

    X. Xu, C. Li, M. Xiong, Z. Tao and Y. Pan, Chem. Commun., 2017, 53, 6219
    DOI: 10.1039/C7CC02484C

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