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 5 2015
Accepted
27 6 2015
First published
03 7 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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