Synthetic Access to Fluorocyclopropylidenes

Organic Letters 2023
Renāte Melngaile, Melita Videja, Jānis Kūka, Artis Kinēns, Dzintars Zacs, Jānis Veliks

Herein we report an approach for the straightforward preparation of fluorocyclopropylidene group from aldehydes and ketones via Julia-Kocienski olefination using the newly developed reagent 5-((2-fluorocyclopropyl)sulfonyl)-1-phenyl-1H-tetrazole. Derivatization of monofluorocyclopropylidene compounds includes hydrogenation to deliver fluorocyclopropylmethyl compounds and fluorinated cyclobutanones. The utility of the described method is demonstrated by the synthesis of a fluorocyclopropyl-containing analogue of ibuprofen. Bioisosteric replacement of isobutyl with the fluorocyclopropyl group may be used for tuning biological properties of drug molecules.

Keywords
Aldehydes, Ketones, Molecular structure, Reaction products, Reagents
DOI
10.1021/acs.orglett.3c00579
Hyperlink
https://pubs.acs.org/doi/10.1021/acs.orglett.3c00579

Melngaile, R., Videja, M., Kūka, J., Kinēns, A., Zacs, D., Veliks, J. Synthetic Access to Fluorocyclopropylidenes. Organic Letters, 2023, Vol. 25, No. 13, pp.2280-2284. ISSN 1523-7060. e-ISSN 1523-7052. Available from: doi:10.1021/acs.orglett.3c00579

Publication language
English (en)