Domino Synthesis of Fluorine-Substituted Polycyclic Aromatic Hydrocarbons: 1,1-Difluoroallenes as Synthetic Platforms

被引:78
作者
Fuchibe, Kohei [1 ]
Mayumi, Yuka [1 ]
Zhao, Nan [1 ]
Watanabe, Shumpei [1 ]
Yokota, Misaki [1 ]
Ichikawa, Junji [1 ]
机构
[1] Univ Tsukuba, Div Chem, Fac Pure & Appl Sci, Tsukuba, Ibaraki 3058571, Japan
关键词
allenes; arenes; cyclization; fluorine; indium; CRAFTS-TYPE CYCLIZATION; FACILE SYNTHESIS; INDIUM TRIBROMIDE; CATALYST SYSTEM; ALDEHYDES; ACTIVATION; CHEMISTRY; ALKYNYLATION; ALCOHOLS; ALKYNES;
D O I
10.1002/anie.201302740
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
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. Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码:7825 / 7828
页数:4
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