Palladium‐Based Dyotropic Rearrangement Enables A Triple Functionalization of Gem‐Disubstituted Alkenes: An Unusual Fluorolactonization Reaction

• Published in: Angewandte Chemie International Edition Vol. 63; no. 1; pp. e202316393 - n/a
• Main Authors: Feng, Qiang, Liu, Chen‐Xu, Wang, Qian, Zhu, Jieping
• Format: Journal Article
• Language: English
• Published: WEINHEIM Wiley 02.01.2024; Wiley Subscription Services, Inc
• Edition: International ed. in English
• Subjects: 1-Fluoroalkylcarboxylate; Acetic acid; Alkenes; Carbon; Carboxylic acids; Chemistry; Chemistry, Multidisciplinary; Dyotropic Rearrangement; Fluorination; Fluorolactonization; High Valent Palladium; Oxidation; Palladium; Physical Sciences; Room temperature; Science & Technology; Dyotropic Rearrangement; High Valent Palladium; SYMMETRY CONTROLLED REACTIONS; DIACETOXYLATION; C-H FLUORINATION; Fluorolactonization; LACTONIZATION; Fluorination; DERIVATIVES; 1-Fluoroalkylcarboxylate; CARBOXYLIC-ACIDS; DIFLUORINATION

We report in this paper a Pd(II)‐catalyzed migratory gem‐fluorolactonization of ene‐carboxylic acids. Reaction of 4‐methylenealkanoic acid derivatives with Selectfluor in the presence of Pd(OAc)2 (1.0 mol %) at room temperature affords fluorolactones in good to excellent yields. 2‐(2‐Methylenecycloa...