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Reactions of fluoroalkanes with Mg-Mg bonds: scope, sp3C-F / sp2C-F coupling and mechanism

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Title: Reactions of fluoroalkanes with Mg-Mg bonds: scope, sp3C-F / sp2C-F coupling and mechanism
Authors: Crimmin, MR
Coates, G
Bakewell, C
Ward, B
White, A
Item Type: Journal Article
Abstract: sp3C-F bonds of fluoroalkanes (7 examples; 1o, 2o and 3o) undergo addition to a low-valent Mg-Mg species generating reactive organomagnesium reagents. Further reactions with a series of electrophiles results in a net C-F to C-B, C-Si, C-Sn or C-C bond transformation (11 examples, diversity). The new reactivity has been exploited in an unprecedented one-pot magnesium-mediated coupling of sp3C-F and sp2C-F bonds. Calculations suggest that the sp3C-F bond activation step occurs by frontside nucleophilic attack of the Mg-Mg reagent on the fluoroalkane.
Issue Date: 2-Nov-2018
Date of Acceptance: 12-Sep-2018
URI: http://hdl.handle.net/10044/1/64442
DOI: https://dx.doi.org/10.1002/chem.201804580
ISSN: 0947-6539
Publisher: Wiley
Start Page: 16282
End Page: 16286
Journal / Book Title: Chemistry - A European Journal
Volume: 24
Issue: 61
Copyright Statement: © 2018 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim. This is the accepted version of the following article: G. Coates, B. J. Ward, C. Bakewell, A. J. P. White, M. R. Crimmin, Chem. Eur. J. 2018, 24, 16282., which has been published in final form at https://dx.doi.org/10.1002/chem.201804580
Sponsor/Funder: The Royal Society
Commission of the European Communities
Funder's Grant Number: UF090149
677367
Keywords: C−F activation
cross-coupling
fluorocarbons
nucleophilic substitution
organomagnesium reagents
C-F activation
Grignard
fluorocarbons: SN2
organomagnesium
03 Chemical Sciences
General Chemistry
Publication Status: Published
Conference Place: Germany
Embargo Date: 2019-09-12
Online Publication Date: 2018-09-12
Appears in Collections:Chemistry
Faculty of Natural Sciences



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