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


Allemann, Oliver; Baldridge, Kim K; Siegel, Jay S (2015). Intramolecular C–H insertion vs. Friedel–Crafts coupling induced by silyl cation-promoted C–F activation. Organic Chemistry Frontiers, 2(9):1018-1021.

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.

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.

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Additional indexing

Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Language:English
Date:2015
Deposited On:11 Apr 2016 13:16
Last Modified:12 Apr 2016 07:40
Publisher:Royal Society of Chemistry
ISSN:2052-4110
Free access at:Publisher DOI. An embargo period may apply.
Publisher DOI:https://doi.org/10.1039/C5QO00170F

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