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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
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 | ||||||
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| 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: |
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| 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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