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Dr. Kohei Fuchibe, Yuka Mayumi, Nan Zhao, Shumpei Watanabe, Dr. Misaki Yokota and Prof. Dr. Junji Ichikawa Domino Synthesis of Fluorine-Substituted Polycyclic Aromatic Hydrocarbons: 1,1-Difluoroallenes as Synthetic Platforms Angewandte Chemie International Edition 52

Article first published online: 14 JUN 2013 | DOI: 10.1002/anie.201302740

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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.

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