Friedel-Crafts-type cyclization of 2,2-difluorovinyl ketones via alpha-fluorocarbocations and its application in domino cyclizations |
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| Authors: | Ichikawa Junji Kaneko Mikio Yokota Misaki Itonaga Masaaki Yokoyama Takaharu |
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| Affiliation: | Department of Chemistry, Graduate School of Science, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo 113-0033, Japan. junji@chem.s.u-tokyo.ac.jp |
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| Abstract: | [Structure: see text] 2,2-Difluorovinyl ketones bearing an aryl group undergo Friedel-Crafts-type cyclization via carbocations stabilized by alpha-fluorines on treatment with a trimethylsilylating agent [Me3SiOTf or Me3SiB(OTf)4]. The reaction affords 4-fluorinated 3-acyl-1,2-dihydronaphthalenes, which are successfully subjected to a substitution-cyclodehydration process or a Nazarov-type cyclization to construct fused polycyclic systems. |
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