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Unravelling nucleophilic aromatic substitution pathways with bimetallic nucleophiles

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Title: Unravelling nucleophilic aromatic substitution pathways with bimetallic nucleophiles
Authors: Garcon, M
Bakewell, C
White, AJP
Crimmin, MR
Item Type: Journal Article
Abstract: The reaction of a metal complex containing a polar Fe–Mg bond with 2-(pentafluorophenyl)pyridine leads to selective C–F bond activation. A stepwise SNAr mechanism involving attack of the bimetallic nucleophile on the electron-deficient aromatic ring has been identified by DFT calculations. Despite the long and rich history of metal anions in organic synthesis, this is the first time the SNAr mechanism has been elucidated in detail for metal-based nucleophiles.
Issue Date: 11-Feb-2019
Date of Acceptance: 14-Jan-2019
URI: http://hdl.handle.net/10044/1/66723
DOI: https://dx.doi.org/10.1039/c8cc09701a
ISSN: 1359-7345
Publisher: Royal Society of Chemistry
Start Page: 1805
End Page: 1808
Journal / Book Title: Chemical Communications
Volume: 55
Issue: 12
Copyright Statement: © 2019 The Royal Society of Chemistry.
Sponsor/Funder: Commission of the European Communities
Funder's Grant Number: 677367
Keywords: Science & Technology
Physical Sciences
Chemistry, Multidisciplinary
Chemistry
METAL-CARBONYL CHEMISTRY
C-F
BOND ACTIVATION
OXIDATIVE ADDITION
MG-MG
ANIONS
PERFLUOROCARBONS
INTERMEDIATE
FLUOROARENES
03 Chemical Sciences
Organic Chemistry
Publication Status: Published
Embargo Date: 2020-01-14
Online Publication Date: 2019-01-14
Appears in Collections:Chemistry
Faculty of Natural Sciences



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