Issue 5, 2015

Remote functionalization of hydrocarbons with reversibility enhanced stereocontrol

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

Supplementary files

Article information

Article type
Edge Article
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
Creative Commons BY license

Chem. Sci., 2015,6, 2770-2776

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

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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