Synthesis of 4,4-Difluoroalkenes by Coupling of α‑Substituted α,α-Difluoromethyl Halides with Allyl Sulfones under Photoredox Catalyzed Conditions

Photoredox-catalyzed allylation of α-gem-difluorinated organohalides with allyl sulfones proceeded smoothly under visible light irradiation to give 4,4-difluoroalkenes in good yields. In the presence of catalytic Ru­(bpy)3Cl2, Hantzsch ester, and diisopropylethylamine, the reaction was complete with...

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Veröffentlicht in:Journal of organic chemistry 2019-07, Vol.84 (14), p.9330-9338
Hauptverfasser: Uno, Misae, Sumino, Shuhei, Fukuyama, Takahide, Matsuura, Makoto, Kuroki, Yoshichika, Kishikawa, Yosuke, Ryu, Ilhyong
Format: Artikel
Sprache:eng
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Zusammenfassung:Photoredox-catalyzed allylation of α-gem-difluorinated organohalides with allyl sulfones proceeded smoothly under visible light irradiation to give 4,4-difluoroalkenes in good yields. In the presence of catalytic Ru­(bpy)3Cl2, Hantzsch ester, and diisopropylethylamine, the reaction was complete within 2 h. Using the same methodology, three-component cascade reactions to give 6,6-difluoroalkenes were carried out successfully.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.9b00901