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Organometallic chemistry using partially fluorinated benzenes

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Pike, Sebastian D., Crimmin, Mark R. and Chaplin, Adrian B. (2017) Organometallic chemistry using partially fluorinated benzenes. Chemical Communications, 53 (26). pp. 3615-3633. doi:10.1039/C6CC09575E ISSN 1359-7345.

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Official URL: http://dx.doi.org/10.1039/C6CC09575E

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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.

Item Type: Journal Article
Subjects: Q Science > QD Chemistry
Divisions: Faculty of Science, Engineering and Medicine > Science > Chemistry
Library of Congress Subject Headings (LCSH): Organometallic chemistry, Benzene, Fluorides , Transition metals , Solvents
Journal or Publication Title: Chemical Communications
Publisher: Royal Society of Chemistry
ISSN: 1359-7345
Official Date: 17 March 2017
Dates:
DateEvent
17 March 2017Published
23 January 2017Available
Volume: 53
Number: 26
Page Range: pp. 3615-3633
DOI: 10.1039/C6CC09575E
Status: Peer Reviewed
Publication Status: Published
Access rights to Published version: Restricted or Subscription Access
Date of first compliant deposit: 3 May 2017
Date of first compliant Open Access: 17 March 2018
Funder: Herchel Smith Chair of Biochemistry Fund, Royal Society (Great Britain), European Research Council (ERC)
Grant number: Starting Grants 677367 and 637313 (ERC)

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