Nickel-Catalyzed Negishi-Type Arylation of Trialkylsulfonium Salts

Hiroko Minami; Keisuke Nogi; Hideki Yorimitsu

doi:10.1055/s-0040-1707817

Synlett, Inhaltsverzeichnis

Synlett 2021; 32(15): 1542-1546
DOI: 10.1055/s-0040-1707817

cluster

Modern Nickel-Catalyzed Reactions

Nickel-Catalyzed Negishi-Type Arylation of Trialkylsulfonium Salts

Authors

Hiroko Minami
Keisuke Nogi
Hideki Yorimitsu ∗

Abstract

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Abstract

Negishi-type arylation of trialkylsulfonium salts with arylzinc reagents has been accomplished under nickel catalysis. The use of cyclohexanethiol as an additional ligand was found to be particularly important to promote C–S cleavage. The present reaction accommodates one-pot arylation of dialkyl sulfides by combining with S-methylation with MeOTf. Mechanistic experiments suggest that C–S cleavage would proceed via single-electron transfer (SET) to generate the most stable carbon-centered radical and that the thiolate ligand would promote the C–S cleavage and radical recombination step.

Key words

Negishi coupling - trialkylsulfonium salt - nickel catalysis - thiolate ligand - radical

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Referenzen

References and Notes

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17 4-Dodecylanisole (3aa) – Typical Procedure for One-Pot Arylation A 10 mL Schlenk tube was charged with dodecyl methyl sulfide (4a, 0.11 g, 0.50 mmol) and DCE (1.0 mL) before an addition of MeOTf (74 μL, 0.65 mmol). The resulting mixture was stirred for 12 h at 60 °C. After removal of all volatiles under reduced pressure (ca. 1 Torr), NiCl₂(bpy) (7.1 mg, 0.025 mmol), CySH (6 μL, 0.050 mmol), and DMA (3.0 mL) were subsequently added to the tube. The resulting mixture was cooled to 0 °C, and a solution of 4-methoxyphenylzinc (2a, 0.56 M in THF, 1.8 mL, 1.0 mmol) was then added dropwise. The resulting mixture was stirred for 12 h at 0 °C before an addition of aqueous HCl (2 M). The resulting biphasic solution was extracted with a mixture of hexane and EtOAc (v/v = 10:1, 3 × 10 mL). The combined organic layer was dried over MgSO₄, filtered, and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: hexane/EtOAc = 100:1) to give 3aa (0.11 g, 0.41 mmol, 82%) as a colorless oil. All the resonances in ¹H NMR and ¹³C NMR spectra were consistent with the reported values in the literature: Komeyama K, Ohata R, Kiguchi S, Osaka I. Chem. Commun. 2017; 53: 6401
18 Ethyl 6-(4-Methoxyphenyl)hexanoate (3ba) Colorless oil (76 mg, 0.30 mmol, 60%). ¹H NMR (594 MHz): δ = 7.08 (d, J = 8.8 Hz, 2 H), 6.82 (d, J = 8.8 Hz, 2 H), 4.12 (q, J = 7.3 Hz, 2 H), 3.79 (s, 3 H), 2.55 (t, J = 7.5 Hz, 2 H), 2.28 (t, J = 7.5 Hz, 2 H), 1.68–1.57 (m, 4 H), 1.38–1.33 (m, 2 H), 1.25 (t, J = 7.3 Hz, 3 H). ¹³C NMR (149 MHz): δ = 174.0, 157.8, 134.8, 129.4, 113.8, 60.3, 55.4, 34.9, 34.4, 31.5, 28.8, 25.0, 14.4. HRMS (APCI-MS, positive): m/z calcd for C₁₅H₂₃O₃: 251.1642 [M + H]⁺; found: 251.1645.
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Zusatzmaterial

Supporting Information (PDF)