Single C−F Bond Activation of the CF 3  Group with a Lewis Acid: CF 3 ‐Cyclopropanes as Versatile 4,4‐Difluorohomoallylating Agents | Zendy

Fuchibe Kohei | Zendy; Oki Rie | Zendy; Hatta Hibiki | Zendy; Ichikawa Junji | Zendy

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Single C−F Bond Activation of the CF 3 Group with a Lewis Acid: CF 3 ‐Cyclopropanes as Versatile 4,4‐Difluorohomoallylating Agents

Author(s) -

Fuchibe Kohei,

Oki Rie,

Hatta Hibiki,

Ichikawa Junji

Publication year - 2018

Publication title -

chemistry – a european journal

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.687

H-Index - 242

eISSN - 1521-3765

pISSN - 0947-6539

DOI - 10.1002/chem.201805054

Subject(s) - silylation , chemistry , nucleophile , lewis acids and bases , enol , ring (chemistry) , group (periodic table) , alkyl , medicinal chemistry , fluoride , trifluoromethyl , stereochemistry , catalysis , organic chemistry , inorganic chemistry

The selective activation of one C−F bond (single activation) of the CF 3 group on cyclopropanes was achieved for the first time. When (trifluoromethyl)cyclopropanes were treated with arenes, allylsilanes, silyl enol ethers, or hydrosilanes in the presence of Me 2 AlCl, fluoride elimination and the subsequent ring opening proceeded to afford 4,4‐difluorohomoallylated products. In the absence of external nucleophiles, an alkyl group of AlR 3 was effectively introduced to provide the corresponding 1,1‐difluoroalkenes.

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