Solid-State Silver-Catalyzed Ring-Opening Fluorination of Cyclobutanols by Using Mechanochemistry

Abstract

In this report, we demonstrate that a ball-milling technique facilitates fast and efficient silver-catalyzed ring-opening fluorination of cyclobutanols. This is the first report of a catalytic C–C bond-cleavage/functionalization reaction under solid-state mechanochemical conditions. The developed protocol affords a high yield of γ-fluorinated ketones within much shorter reaction times, and requires less silver catalyst and Selectfluor compared with the previous solution-based conditions. Notably, the process can be carried out in air. Because of the reduced use of chemicals and the simple time-saving experimental procedures, this technique is an efficient and environmentally friendly way to access γ-fluorinated ketones.

Key words

C–C bond cleavage - fluorination - mechanochemistry - ball-milling - solid-state chemistry - silver catalysis

Publikationsverlauf

Eingereicht: 18. November 2022

Angenommen nach Revision: 29. Januar 2023

Accepted Manuscript online:
29. Januar 2023

Artikel online veröffentlicht:
03. Mai 2023

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• 15 4-Fluoro-1-phenylbutan-1-one (2a); Typical Procedure Cyclobutanol 1A (44.3 mg, 0.30 mmol, 1.0 equiv), AgF (1.9 mg, 0.015 mmol, 5.0 mol%), and Selectfluor (107.2 mg, 0.30 mmol, 1.0 equiv) were placed in a ball-milling vessel (ZrO₂, 10 mL) loaded with one grinding ball (ZrO₂; diameter: 10 mm). H₂O (31 μL, 0.20 μL/mg) was added from a syringe. The vessel was then closed in air without purging with an inert gas, and placed in the ball mill (Retsch MM400) for 30 min at 15 Hz with heating by a heat gun to an internal temperature of 55 °C. After 30 min, H₂O and Et₂O were added and the mixture was extracted with Et₂O (×3). The combined organic layer was dried (MgSO₄), filtered, and concentrated in vacuo. The crude product was purified by flash column chromatography [silica gel, hexane–EtOAc, 50:1] to give a colorless oil; yield: 33.8 mg (68%). ¹H NMR (400 MHz, CDCl₃): δ = 2.16 (d quint, J = 27.6, 6.4 Hz, 2 H), 3.16 (t, J = 6.4 Hz, 2 H), 4.57 (dt, J = 48.8, 6.4 Hz, 2 H), 7.48 (t, J = 8.0 Hz, 2 H), 7.58 (t, J = 8.0 Hz, 1 H), 7.99 (d, J = 8.0 Hz, 2 H). ¹³C NMR (101 MHz CDCl₃): δ = 24.8 (d, J _C–F = 20.2 Hz, CH₂), 33.9 (d, J _C–F = 4.8 Hz, CH₂), 83.3 (d, J _C–F = 165.9 Hz, CH₂), 127.9 (CH), 128.6 (CH), 133.1 (CH), 136.7 (C), 199.0 (C). ¹⁹F NMR (376 MHz CDCl₃): δ = –220.9 to –221.4 (m, 1 F). HRMS-EI: m/z [M]⁺ calcd for C₁₀H₁₁FO: 166.07939; found: 166.07934. The NMR spectra agreed with those reported in the literature.^8h