Copper-Catalyzed Production of Diaryl Sulfides Using Aryl Iodides and a Disilathiane

Yohei Ogiwara; Hiromu Maeda; Norio Sakai

doi:10.1055/s-0036-1591723

Synlett, Inhaltsverzeichnis

Synlett 2018; 29(05): 655-657
DOI: 10.1055/s-0036-1591723

letter

Copper-Catalyzed Production of Diaryl Sulfides Using Aryl Iodides and a Disilathiane

Yohei Ogiwara

Department of Pure and Applied Chemistry, Faculty of Science and Technology, Tokyo University of Science, 2641 Yamazaki, Noda, Chiba 278-8510, Japan eMail: sakachem@rs.noda.tus.ac.jp

,

Hiromu Maeda

Department of Pure and Applied Chemistry, Faculty of Science and Technology, Tokyo University of Science, 2641 Yamazaki, Noda, Chiba 278-8510, Japan eMail: sakachem@rs.noda.tus.ac.jp

,

Norio Sakai*

Department of Pure and Applied Chemistry, Faculty of Science and Technology, Tokyo University of Science, 2641 Yamazaki, Noda, Chiba 278-8510, Japan eMail: sakachem@rs.noda.tus.ac.jp

› Institutsangaben

Abstract

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Abstract

A disilathiane was found to be a novel S1 source for the copper-catalyzed synthesis of diaryl sulfides using aryl iodides. The reaction of iodoarenes and hexamethyldisilathiane, (Me₃Si)₂S, in the presence of a catalytic amount of CuI/1,10-phenanthroline provided various types of diaryl sulfides in good yields.

Key words

copper catalyst - aryl iodides - disilathiane - carbon–sulfur bond formation - diaryl sulfides

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Referenzen

References and Notes

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14 General Procedure To a screw-capped test tube under a nitrogen atmosphere, 1,10-phenanthroline (0.05 mmol, 9.0 mg), iodobenzene 1 (1 mmol), K₂CO₃ (1 mmol, 138.2 mg), CuI (0.05 mmol, 9.5 mg), N-methyl-2-pyrrolidone (1 mL), and 1,1,1,3,3,3-hexamethyldisilathiane (0.5 mmol, 89.2 mg) were added. After the tube was sealed with a cap, the mixture was heated at 120 °C for 14 h. After the reaction, H₂O was added to the mixture, which was then extracted with EtOAc three times. The combined organic phases were evaporated under reduced pressure. The crude material was purified by silica gel column chromatography to give the corresponding diaryl sulfide 2. Diphenyl Sulfide (2a) The general procedure was followed with iodobenzene (1a, 202.7 mg, 0.99 mmol) for 14 h. Column chromatography (hexane) afforded 2a as a colorless oil (85.0 mg, 92%). ¹H NMR (500.2 MHz, CDCl₃): δ = 7.23 (t, J = 7.5 Hz, 2 H, ArH), 7.29 (t, J = 7.5 Hz, 4 H, ArH), 7.34 (d, J = 7.5 Hz, 4 H, ArH). ¹³C NMR (125.8 MHz, CDCl₃): δ = 127.0, 129.2, 131.0, 135.8. LRMS (EI): m/z (% relative intensity) = 187 (17) [M + 1]⁺, 186 (100), 185 (69), 184 (27), 154 (14), 134 (14), 77 (15), 51 (20).
15 An alkyl iodide was also applicable for this reaction (Scheme 4).
16 See the Supporting Information for further results to support the proposed mechanism.

Zusatzmaterial

Supporting Information