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Issue 26, 2017
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Organometallic chemistry using partially fluorinated benzenes

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Abstract

Fluorobenzenes, in particular fluorobenzene (FB) and 1,2-difluorobenzene (1,2-DiFB), are increasingly becoming recognised as versatile solvents for conducting organometallic chemistry and transition-metal-based catalysis. The presence of fluorine substituents reduces the ability to donate π-electron density from the arene and consequently fluorobenzenes generally bind weakly to metal centres, allowing them to be used as essentially non-coordinating solvents or as readily displaced ligands. In this context, examples of well-defined complexes of fluorobenzenes are discussed, including trends in binding strength with increasing fluorination and different substitution patterns. Compared to more highly fluorinated benzenes, FB and 1,2-DiFB typically demonstrate greater chemical inertness, however, C–H and C–F bond activation reactions can be induced using appropriately reactive transition metal complexes. Such reactions are surveyed, including catalytic examples, not only to provide perspective for the use of FB and 1,2-DiFB as innocent solvent media, but also to highlight opportunities for their exploitation in contemporary organic synthesis.

Graphical abstract: Organometallic chemistry using partially fluorinated benzenes

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Article information


Submitted
01 Dec 2016
Accepted
23 Jan 2017
First published
17 Mar 2017

Chem. Commun., 2017,53, 3615-3633
Article type
Feature Article

Organometallic chemistry using partially fluorinated benzenes

S. D. Pike, M. R. Crimmin and A. B. Chaplin, Chem. Commun., 2017, 53, 3615
DOI: 10.1039/C6CC09575E

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