Transition-Metal-Free Efficient Synthesis of Bisindole Sulfanes Using 2-(Fluorosulfonyl)difluoroacetic Acid

Yang Li; Lan-Ting Shi; Wen-Qing Zhu; Hong Li; Qiang Zhang

doi:10.1055/s-0037-1609573

Synlett, Inhaltsverzeichnis

Synlett 2018; 29(14): 1847-1850
DOI: 10.1055/s-0037-1609573

letter

Transition-Metal-Free Efficient Synthesis of Bisindole Sulfanes Using 2-(Fluorosulfonyl)difluoroacetic Acid

Yang Li *

^aSchool of Environmental and Chemical Engineering, Xi’an Polytechnic University, Xi'an 710048, P. R. of China eMail: liyang@xpu.edu.cn

,

Lan-Ting Shi

^aSchool of Environmental and Chemical Engineering, Xi’an Polytechnic University, Xi'an 710048, P. R. of China eMail: liyang@xpu.edu.cn

,

Wen-Qing Zhu

^aSchool of Environmental and Chemical Engineering, Xi’an Polytechnic University, Xi'an 710048, P. R. of China eMail: liyang@xpu.edu.cn

,

Hong Li

^aSchool of Environmental and Chemical Engineering, Xi’an Polytechnic University, Xi'an 710048, P. R. of China eMail: liyang@xpu.edu.cn

,

Qiang Zhang

^bSchool of Chemistry and Environmental Science, Shaanxi University of Technology, Shaanxi Key Laboratory of Catalysis, Hanzhong 723001, P. R. of China

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Abstract

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Abstract

By using 2-(fluorosulfonyl)difluoroacetic acid as sulfur reagent, bisindole sulfanes were highly efficient synthesized under transition-metal-free conditions. Results indicate that this proceeded not at the relatively acidic C-2 position but rather selectively at the nucleophilic C-3 position to give the desired compounds with excellent regioselectivities and good yields.

Key words

synthesis - indoles - 2-(fluorosulfonyl)difluoroacetic acid - sulfur reagent - bisindole sulfanes

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Referenzen

References and Notes

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20 General Procedure for the Synthesis of 3i The reaction was carried out in an autoclave containing a 35 mL Teflon reaction tube. 1-Methyl-1H-indole-5-carbonitrile (156 mg, 1.0 mmol), NaHCO₃ (168 mg, 2.0 mmol), DMF (2.0 mL), and a magnetic stir bar were placed in the tube, which was then stirred under air. Then, 2-(fluorosulfonyl)difluoroacetic acid (356 mg, 2.0 mmol) was added to the tube one pot. The reaction temperature rose from 25 °C to 110 °C in 10 s and some of gas emitted. After the addition, the reaction tube was then cooled down to r.t., water (40 mL) was added, and the product was extracted with DCM (3 × 15 mL). The organic layers were washed with brine, dried over Na₂SO₄, and evaporated the organic solvent by rotatory evaporator under atmospheric pressure. The crude product was purified by column chromatography (silica gel, petroleum ether/ethyl acetate as eluent). Compound 3i: Colorless oil (103 mg, 60%). R_f = 0.2 (petroleum ether/ethyl acetate = 4:1). ¹H NMR (500 MHz, DMSO-d ₆): δ = 8.23 (s, 2 H), 8.03 (s, 2 H), 7.63 (d, 2 H, J = 8.5 Hz), 7.53 (d, 2 H, J = 8.5 Hz), 3.81 (s, 6 H). ¹³C NMR (125 MHz, DMSO-d ₆): δ = 138.9, 137.4, 128.9, 125.1, 124.4, 120.8, 112.4, 105.5, 102.6, 33.4. IR (KBr): 3057, 2915, 2245, 1750, 1636, 1311, 1114, 1058, 774, 739 cm^–1. HRMS (ESI): m/z calcd for [M + H⁺]: 343.1017; found: 343.1015.
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