Silver-Catalyzed Ring-Opening Strategy for the Synthesis of β- and γ‑Fluorinated Ketones

• Published in: Journal of the American Chemical Society Vol. 137; no. 10; pp. 3490 - 3493
• Main Authors: Zhao, Huijun, Fan, Xuefeng, Yu, Jiajia, Zhu, Chen
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 18.03.2015; Amer Chemical Soc
• Subjects: Chemistry; Chemistry, Multidisciplinary; Physical Sciences; Science & Technology; MEDICINAL CHEMISTRY; COPPER-MEDIATED FLUORINATION; BENZYLIC FLUORINATION; C-H FLUORINATION; ENANTIOSELECTIVE FLUORINATION; LATE-STAGE; PHASE-TRANSFER CATALYST; BOND FORMATION; ARYL FLUORIDES; UNACTIVATED ALKENES

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 introduct...