Issue 9, 2015

Intramolecular C–H insertion vs. Friedel–Crafts coupling induced by silyl cation-promoted C–F activation

Abstract

Silyl cation-promoted aryl C–F activation can lead to formal C–H activation and the formation of new C(ar)–C(alkyl) bonds. Deuterium-labeling experiments suggest an insertion of a phenyl cation into the C–H bond. From competition experiments, a relation between reaction rate and C–H bond strength could be established. Mechanistic parallels are drawn to the Mascarelli reaction.

Graphical abstract: Intramolecular C–H insertion vs. Friedel–Crafts coupling induced by silyl cation-promoted C–F activation

Supplementary files

Article information

Article type
Research Article
Submitted
27 mai 2015
Accepted
27 jun 2015
First published
03 jul 2015
This article is Open Access
Creative Commons BY license

Org. Chem. Front., 2015,2, 1018-1021

Author version available

Intramolecular C–H insertion vs. Friedel–Crafts coupling induced by silyl cation-promoted C–F activation

O. Allemann, K. K. Baldridge and J. S. Siegel, Org. Chem. Front., 2015, 2, 1018 DOI: 10.1039/C5QO00170F

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