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Organometallic chemistry using partially fluorinated benzenes

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Title: Organometallic chemistry using partially fluorinated benzenes
Authors: Pike, SD
Crimmin, MR
Chaplin, AB
Item Type: Journal Article
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 available π-electron density 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.
Issue Date: 17-Mar-2017
Date of Acceptance: 23-Jan-2017
URI: http://hdl.handle.net/10044/1/44196
DOI: https://dx.doi.org/10.1039/c6cc09575e
ISSN: 1364-548X
Publisher: Royal Society of Chemistry
Start Page: 3615
End Page: 3633
Journal / Book Title: Chemical Communications
Volume: 53
Copyright Statement: This journal is © The Royal Society of Chemistry 2017
Sponsor/Funder: The Royal Society
Commission of the European Communities
Commission of the European Communities
Funder's Grant Number: UF090149
655474
677367
Keywords: Organic Chemistry
03 Chemical Sciences
Publication Status: Published
Appears in Collections:Chemistry
Faculty of Natural Sciences



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