Intermolecular Reductive Radical Addition to 2-(2,2,2-Trifluoroethylidene)-1,3-dithiane 1-Oxide: Experimental and Theoretical Studies

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• 作者：Ryota Nakayama ; Hiroshi Matsubara ; Daishi Fujino ; Takayuki Kobatake ; Suguru Yoshida ; Hideki Yorimitsu ; Koichiro Oshima
• 刊名：Organic Letters
• 出版年：2010
• 出版时间：December 17, 2010
• 年：2010
• 卷：12
• 期：24
• 页码：5748-5751
• 全文大小：263K
• 年卷期：v.12,no.24(December 17, 2010)
• ISSN：1523-7052

文摘

Tin hydride mediated radical addition of organic halide to 2-(2,2,2-trifluoroethylidene)-1,3-dithiane 1-oxide has been devised. The reaction is equivalent to an unrealizable radical addition to trifluoromethylketene, providing useful α-trifluoromethyl carbonyl equivalents. The trifluoromethyl and the sulfoxide groups of the substrate play key roles for the success of the radical addition, lowering the barrier of the radical addition step and controlling the stereoselectivity of the reaction, which DFT calculations have elucidated.