Rather crafty: 1,1-Difluoroallenes bearing an aryl group and a cyclopentene moiety undergo indium(III)-catalyzed Friedel-Crafts-type cyclization with subsequent ring expansion and dehydrogenation to afford fluorinated polycyclic aromatic hydrocarbons in high yields. The introduction of an Ar group was effected by in situ halogenation of the intermediary indium species and a subsequent Suzuki-Miyaura reaction.
Dominoeffekt: 1,1‐Difluorallene mit einem Aryl‐ und einem Cyclopentenring reagieren in Indium(III)‐katalysierten Friedel‐Crafts‐Cyclisierungen mit anschließender Ringerweiterung und Dehydrierung in hohen Ausbeuten zu fluorierten polycyclischen aromatischen Kohlenwasserstoffen. Die Einführung einer Ar‐Gruppe gelang durch In‐situ‐Halogenierung der intermediären Indiumspezies und anschließende Suzuki‐Miyaura‐Kupplung.
1,1-Difluoroallenes underwent β-selective C–C bond formation (insertion) via π-allylpalladium(ii) to facilitate aromatic ring construction, leading to biologically promising (difluoromethyl)naphthalenes.
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