†Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science, Soochow University, 199 Ren-Ai Road, Suzhou, Jiangsu 215123, People's Republic of China.
‡Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, People's Republic of China.
J Am Chem Soc. 2015 Mar 18;137(10):3490-3. doi: 10.1021/jacs.5b00939. Epub 2015 Mar 5.
A regioselective synthesis of β- and γ-fluorinated ketones via silver-catalyzed ring opening is described. A variety of β- and γ-fluorinated ketones are efficiently prepared, respectively, from tertiary cyclopropanol and cyclobutanol precursors, providing a straightforward approach for the introduction of a fluorine atom into complex molecules. Preliminary mechanistic studies suggest that a radical-mediated sequential C-C bond cleavage and C-F bond formation pathway is involved.
本文描述了一种通过银催化开环反应实现β-和γ-氟代酮的区域选择性合成的方法。通过叔环丙烷和环丁醇前体，分别高效制备了各种β-和γ-氟代酮，为在复杂分子中引入氟原子提供了一种直接的方法。初步的机理研究表明，该反应涉及自由基介导的顺序 C-C 键断裂和 C-F 键形成途径。
