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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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Article information


Submitted
05 Feb 2015
Accepted
03 Mar 2015
First published
03 Mar 2015

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2015,6, 2770-2776
Article type
Edge Article
Author version available

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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