α-フルオロビニル基を有するビルディングブロックの開発と合成化学的利用
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概要
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We prepared and examined several versatile mono-fluorinated building blocks bearing an α-fluorovinyl moiety. Each compound has a variety of heteroatoms such as phosphorus, silicon, stannane, and sulfur. This review mainly consists of the following four parts. 1) (α-Fluorovinyl) phosphonium salts underwent Michael addition followed by Wittig olefination to give the corresponding monofluoroethylene compounds in good yields. 2) α-Fluorovinylation with carbonyl compounds was carried out using (α-fluorovinyl) methyldiphenylsilane in the presence of TBAF. 3) Cross-coupling reaction of the silane with aryl halides smoothly proceeded giving the corresponding α-fluorinated styrene derivatives. 4) Carbonylative cross-coupling reaction of (α-fluorovinyl)tributylstannane with aryl halides and aryl triflates proceeded to afford the corresponding α-fluorovinyl aryl ketones under a CO atmosphere. Finally, 1, 1-difluoroethylene as a key fluoride source was employed in order to prepare the above building blocks.
- 社団法人 有機合成化学協会の論文
- 2002-12-01