Ben J. Murray
HFO-1234yf as a CF3-building block: Synthesis of trifluoromethyl-benzophenone derivatives by deoxygenative aromatisation
Murray, Ben J.; Boulton, Lee T.; Sandford, Graham
Authors
Lee T. Boulton
Graham Sandford
Abstract
Trifluoromethyl ynones derived from the 4th generation refrigerant 2,3,3,3-tetrafluoropropene (HFO-1234yf) undergo rapid Diels-Alder cycloaddition reactions with furans in near quantitative yields. Subsequent deoxygenation of the resulting oxabicyclic adducts leads to formation of ortho-trifluoromethylbenzophenones in generally good yields without the need for purification by column chromatography. Complete selectivity for a single regioisomer was observed in all cases. This method provides a new route from an inexpensive feedstock to highly substituted CF3-aromatic systems that can be difficult to access selectively by established methods.
Citation
Murray, B. J., Boulton, L. T., & Sandford, G. (2021). HFO-1234yf as a CF3-building block: Synthesis of trifluoromethyl-benzophenone derivatives by deoxygenative aromatisation. Journal of Fluorine Chemistry, 245, https://doi.org/10.1016/j.jfluchem.2021.109774
Journal Article Type | Article |
---|---|
Acceptance Date | Mar 9, 2021 |
Online Publication Date | Mar 10, 2021 |
Publication Date | 2021-05 |
Deposit Date | May 18, 2021 |
Publicly Available Date | Mar 10, 2023 |
Journal | Journal of Fluorine Chemistry |
Print ISSN | 0022-1139 |
Publisher | Elsevier |
Peer Reviewed | Peer Reviewed |
Volume | 245 |
DOI | https://doi.org/10.1016/j.jfluchem.2021.109774 |
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http://creativecommons.org/licenses/by-nc-nd/4.0/
Copyright Statement
© 2021 This manuscript version is made available under the CC-BY-NC-ND 4.0 license http://creativecommons.org/licenses/by-nc-nd/4.0/
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