Synthesis of gem‑bromofluoroolefins using singlet bromofluorocarbene generated from ethyl dibromofluoroacetate via a Wittig-type reaction

•Synthesis of gem‑bromofluoroolefins utilizing ethyldibromofluoroacetate and triphenyl- phosphine.•The reaction takes place via a Wittig type intermediate.•The reaction goes through a singlet bromofluorocarbene intermediate.•The reaction works with a wide variety of aryl aldehydes. A halon-free meth...

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Veröffentlicht in:Journal of fluorine chemistry 2024-05, Vol.276, p.110278, Article 110278
Hauptverfasser: Coe, Matthew, Bede, Fanni, Koch, Christopher J., Espiritu, Danelle Daria, Prakash, G.K.Surya
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Sprache:eng
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Zusammenfassung:•Synthesis of gem‑bromofluoroolefins utilizing ethyldibromofluoroacetate and triphenyl- phosphine.•The reaction takes place via a Wittig type intermediate.•The reaction goes through a singlet bromofluorocarbene intermediate.•The reaction works with a wide variety of aryl aldehydes. A halon-free method for the synthesis of gem‑bromofluoroolefins utilizing ethyldibromofluoro-acetate is disclosed via a Wittig type reaction. The reaction system takes advantage of inexpensive and readily available reagents. The method was applied to a wide variety of aryl aldehydes. Both electron donating and electron withdrawing moieties on the aryl ring were tolerated and the desired olefin products were obtained in good to excellent yields. [Display omitted]
ISSN:0022-1139
1873-3328
DOI:10.1016/j.jfluchem.2024.110278