HFO-1234yf as a CF3-building block: Synthesis of trifluoromethyl-benzophenone derivatives by deoxygenative aromatisation

Murray, Ben J.; Boulton, Lee T.; Sandford, Graham

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
• Electronic ISSN: 1873-3328
• Publisher: Elsevier
• Peer Reviewed: Peer Reviewed
• Volume: 245
• DOI: https://doi.org/10.1016/j.jfluchem.2021.109774
• Public URL: https://durham-repository.worktribe.com/output/1247995