Friedel-Crafts-type cyclization of 2,2-difluorovinyl ketones via α-fluorocarbocations and its application in domino cyclizations
Friedel-Crafts-type cyclization of 2,2-difluorovinyl ketones via α-fluorocarbocations and its application in domino cyclizations
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DOI：
10.1021/ol060912r
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发表时间：
2006-07-20
期刊：
影响因子：
5.2
通讯作者：
Yokoyama, Takaharu
中科院分区：
文献类型：
--
作者：
Ichikawa, Junji;Kaneko, Mikio;Yokoyama, Takaharu
带有芳基的2,2-二氟乙烯基酮在三甲基硅化剂的作用下，通过由-氟稳定的碳阳离子发生弗里德尔-克拉夫特型环化[Me3SiOTf或Me3SiB(OTf)(4)]。该反应产生4-氟化3-酰基-1,2-二氢萘，成功地进行取代-环脱水过程或纳扎罗夫型环化以构建融合多环体系。
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.