TMSOTf-Promoted Sulfinylation of Electron-Rich Aromatics with Sodium Arylsulfinates

Yuan-Zhao Ji; Hui-Jing Li; Hao-Ran Yang; Zheng-Yan Zhang; Li-Jun Xie; Yan-Chao Wu

doi:10.1055/s-0039-1691563

Synlett, Inhaltsverzeichnis

Synlett 2020; 31(04): 349-354
DOI: 10.1055/s-0039-1691563

letter

TMSOTf-Promoted Sulfinylation of Electron-Rich Aromatics with Sodium Arylsulfinates

Yuan-Zhao Ji

^aSchool of Marine Science and Technology, Harbin Institute of Technology, 2 Wenhuaxi Road, Weihai 264209, P. R. of China

,

Hui-Jing Li∗

^aSchool of Marine Science and Technology, Harbin Institute of Technology, 2 Wenhuaxi Road, Weihai 264209, P. R. of China

^bWeihai Institute of Marine Biomedical Industrial Technology, Wendeng District, Weihai 264400, P. R. of China eMail: lihuijing@iccas.ac.cn eMail: ycwu@iccas.ac.cn

,

Hao-Ran Yang

^aSchool of Marine Science and Technology, Harbin Institute of Technology, 2 Wenhuaxi Road, Weihai 264209, P. R. of China

,

Zheng-Yan Zhang

^aSchool of Marine Science and Technology, Harbin Institute of Technology, 2 Wenhuaxi Road, Weihai 264209, P. R. of China

,

Li-Jun Xie

^aSchool of Marine Science and Technology, Harbin Institute of Technology, 2 Wenhuaxi Road, Weihai 264209, P. R. of China

,

Yan-Chao Wu ∗

^aSchool of Marine Science and Technology, Harbin Institute of Technology, 2 Wenhuaxi Road, Weihai 264209, P. R. of China

^bWeihai Institute of Marine Biomedical Industrial Technology, Wendeng District, Weihai 264400, P. R. of China eMail: lihuijing@iccas.ac.cn eMail: ycwu@iccas.ac.cn

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Abstract

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Abstract

A new transition-metal-free route for the direct sulfinylation of electron-rich aromatics with sodium arylsulfinates in the presence of TMSOTf is reported. Various electron-rich aromatics, including pyrroles, thiophenes, indoles, and electron-rich arenes, with sodium arylsulfinates are converted into the corresponding sulfoxides in moderate to excellent yields. This protocol possesses many advantages such as readily available and stable starting materials, broad substrate scopes, and transition-metal-free reaction conditions.

Key words

sulfinylation - pyrroles - indoles - sulfoxides - sodium arylsulfinates

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References and Notes

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17 General Procedure for the Preparation of Sulfoxides 4 The mixture of sodium arylsulfinate (0.2 mmol, 1.0 equiv), pyrrole/thiophenes (0.3 mmol, 1.5 equiv), and TMSOTf (0.4 mmol, 2.0 equiv) in (ClCH₂)₂ (1.0 mL) was stirred at 25 °C for 0.5 h. After completion of the reaction, water (5 mL) and dichloromethane (10 mL) were added. The two layers were separated, and the aqueous phase was extracted with dichloromethane (3 × 10 mL). The combined organic extracts were washed by brine, dried over anhydrous Na₂SO₄, filtered, and concentrated. The residue was purified by flash chromatography on silica gel (ethyl acetate–petroleum ether = 1:1) to afford the desired sulfoxides 4. Compound 4a: white solid, mp 84–86 °C; 36.3 mg, 83% yield. ¹H NMR (400 MHz, CDCl₃): δ = 7.53 (d, J = 8.2 Hz, 2 H), 7.27 (d, J = 8.0 Hz, 2 H), 6.95 (t, J = 2.0 Hz, 1 H), 6.58 (t, J = 2.5 Hz, 1 H), 6.16 (dd, J = 3.0, 1.7 Hz, 1 H), 3.64 (s, 3 H), 2.39 (s, 3 H). ¹³C NMR (100 MHz, CDCl₃): δ = 141.9, 140.3, 129.3, 126.8, 124.5, 124.3, 123.9, 107.4, 36.4, 21.2. Data are in accordance to those previously reported.^13a General Procedure for the Preparation of Sulfoxides 10 The mixture of sodium arylsulfinate (0.2 mmol, 1.0 equiv), indole (0.4 mmol, 2.0 equiv), and TMSOTf (0.4 mmol, 2.0 equiv) in (ClCH₂)₂ (1.0 mL) was stirred at 25 °C for 0.5 h. After completion of the reaction, water (5 mL) and dichloromethane (10 mL) were added. The two layers were separated, and the aqueous phase was extracted with dichloromethane (3 × 10 mL). The combined organic extracts were washed by brine, dried over anhydrous Na₂SO₄, filtered, and concentrated. The residue was purified by flash chromatography on silica gel (ethyl acetate–petroleum ether = 1:1) to afford the desired sulfoxides 10. Compound 10a: white solid, mp 138–139 °C; 42.0 mg, 78% yield. ¹H NMR (400 MHz, CDCl₃): δ = 7.62 (d, J = 8.2 Hz, 2 H), 7.48 (d, J = 8.7 Hz, 2 H),7.34–7.24 (m, 4 H), 7.12–7.08 (m, 1 H), 3.79 (s, 3 H), 2.40 (s, 3 H). ¹³C NMR (100 MHz, CDCl₃): δ = 140.9, 140.3, 137.6, 132.5, 129.5, 124.8, 124.3, 123.2, 121.3, 119.8, 116.5, 110.0, 33.2, 21.2. Data are in accordance to those previously reported.^13a General Procedure for the Preparation of Sulfoxides 12 The mixture of sodium arylsulfinate (0.2 mmol, 1.0 equiv), arene (0.4 mmol, 2.0 equiv), and TMSOTf (0.4 mmol, 2.0 equiv) in (ClCH₂)₂ (1.0 mL) was stirred at 25 °C for 1 h. After completion of the reaction, water (5 mL) and dichloromethane (10 mL) were added. The two layers were separated, and the aqueous phase was extracted with dichloromethane (3 × 10 mL). The combined organic extracts were washed by brine, dried over anhydrous Na₂SO₄, filtered, and concentrated. The residue was purified by flash chromatography on silica gel (ethyl acetate–petroleum ether = 1:1) to afford the desired sulfoxides 12. Compound 12a: colorless oil, 27.0 mg, 55% yield. ¹H NMR (400 MHz, CDCl₃): δ = 7.55 (d, J = 8.8 Hz, 2 H), 7.49 (d, J = 8.1 Hz, 2 H), 7.25 (d, J = 7.3 Hz, 2 H), 6.95 (d, J = 8.8 Hz, 2 H), 3.81 (s, 3 H), 2.36 (s, 3 H). ¹³C NMR (100 MHz, CDCl₃): δ = 161.8, 142.5, 141.2, 136.9, 129.8, 127.0, 124.7, 114.7, 55.4, 21.3. Data are in accordance to those previously reported.^11a

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