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Reactions of Fluoroalkenes with an Aluminium(I) Complex.

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Title: Reactions of Fluoroalkenes with an Aluminium(I) Complex.
Authors: Bakewell, C
White, AJP
Crimmin, MR
Item Type: Journal Article
Abstract: A series of industrially relevant fluoroalkenes react with a monomeric AlI complex. These reactions break strong sp2 and sp3 C-F bonds, and result in the formation of a diverse array of organoaluminium compounds. Mechanistic studies show that two mechanisms are likely in operation: 1) direct oxidative addition of the C-F bond to AlI occurs with retention of alkene stereochemistry, and 2) stepwise formation and decomposition of a metallocyclopropane intermediate occurs with inversion of alkene stereochemistry. As part of this mechanistic analysis, we have isolated the first aluminium metallocyclopropane complex from oxidative addition of an alkene to AlI . Remarkably this reaction is reversible and reductive elimination of the alkene occurs at higher temperature reforming AlI . Furthermore, in selected cases the organoaluminium products are susceptible toward β-fluoride elimination to yield a double C-F activation pathway.
Issue Date: 28-May-2018
Date of Acceptance: 12-Apr-2018
URI: http://hdl.handle.net/10044/1/60994
DOI: https://dx.doi.org/10.1002/anie.201802321
ISSN: 1521-3757
Publisher: Wiley
Start Page: 6638
End Page: 6642
Journal / Book Title: Angewandte Chemie International Edition
Volume: 57
Issue: 22
Copyright Statement: © 2018 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim. This is the accepted version of the following article: C. Bakewell, A. J. P. White, M. R. Crimmin, Angew. Chem. Int. Ed. 2018, 57, 6638, which has been published in final form at https://dx.doi.org/10.1002/anie.201802321
Keywords: HFOs
aluminum
fluoride elimination
fluoroolefins
hydrofluorocarbons
03 Chemical Sciences
Organic Chemistry
Publication Status: Published
Conference Place: Germany
Online Publication Date: 2018-05-02
Appears in Collections:Chemistry
Faculty of Natural Sciences



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