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Issue 5, 2015
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Remote functionalization of hydrocarbons with reversibility enhanced stereocontrol

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Abstract

Remote functionalization of hydrocarbons could be achieved through successive zirconocene-mediated allylic C–H bond activations followed by a selective C–C bond cleavage. Determination of the reaction mechanism by density functional theory (DFT) calculations shows that the high stereocontrol observed in this process results from a large number of energetically accessible equilibria feeding a preferred reactive channel that leads to the major product. A distinctive consequence of this pattern is that stereoselectivity is enhanced upon heating.

Graphical abstract: Remote functionalization of hydrocarbons with reversibility enhanced stereocontrol

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Publication details

The article was received on 05 Feb 2015, accepted on 03 Mar 2015 and first published on 03 Mar 2015


Article type: Edge Article
DOI: 10.1039/C5SC00445D
Citation: Chem. Sci., 2015,6, 2770-2776
  • Open access: Creative Commons BY license
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    Remote functionalization of hydrocarbons with reversibility enhanced stereocontrol

    A. Vasseur, L. Perrin, O. Eisenstein and I. Marek, Chem. Sci., 2015, 6, 2770
    DOI: 10.1039/C5SC00445D

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