8-Hydroxyquinolin-N-oxide-Promoted Copper-Catalyzed C–S Cross-Coupling of Thiols with Aryl Iodides

Kun Su; Yatao Qiu; Yiwu Yao; Dayong Zhang; Sheng Jiang

doi:10.1055/s-0032-1317518

Synlett, Inhaltsverzeichnis

Synlett 2012; 23(19): 2853-2857
DOI: 10.1055/s-0032-1317518

letter

8-Hydroxyquinolin-N-oxide-Promoted Copper-Catalyzed C–S Cross-Coupling of Thiols with Aryl Iodides

Kun Su

^aCenter of Drug Discovery, Chinese Pharmaceutical University, Nanjing 210009, P. R. of China Fax: +86(20)32015318 eMail: zhangdayong@cpu.edu.cn

^bLaboratory of Regenerative Biology, Guangzhou Institute of Biomedicine and Health, CAS, Guangzhou 510663, P. R. of China eMail: jiang_sheng@gibh.ac.cn

,

Yatao Qiu

^bLaboratory of Regenerative Biology, Guangzhou Institute of Biomedicine and Health, CAS, Guangzhou 510663, P. R. of China eMail: jiang_sheng@gibh.ac.cn

,

Yiwu Yao

^bLaboratory of Regenerative Biology, Guangzhou Institute of Biomedicine and Health, CAS, Guangzhou 510663, P. R. of China eMail: jiang_sheng@gibh.ac.cn

,

Dayong Zhang*

^aCenter of Drug Discovery, Chinese Pharmaceutical University, Nanjing 210009, P. R. of China Fax: +86(20)32015318 eMail: zhangdayong@cpu.edu.cn

,

Sheng Jiang*

^bLaboratory of Regenerative Biology, Guangzhou Institute of Biomedicine and Health, CAS, Guangzhou 510663, P. R. of China eMail: jiang_sheng@gibh.ac.cn

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Abstract

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Abstract

8-Hydroxyquinolin-N-oxide was identified as a superior ligand for CuI-catalyzed C–S coupling reactions of aryl iodides with thiols to afford the corresponding thioethers in excellent yield. The method shows excellent chemoselectivity and high functional-group tolerance in both coupling partners.

Key words

C–S coupling reactions - copper - cross-coupling - 8-hydroxyquinolin-N-oxide - Ullmann reaction

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Referenzen

References and Notes

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9 General Experimental Procedure An argon-filled flask was charged with CuI (20 mg, 0.1 mmol, 10 mol%), L5 (32 mg, 0.2 mmol, 20 mol%), Cs₂CO₃ (652 mg, 2 mmol, and thiophenol (1 mmol). The aryl iodide (1.5 mmol) and DMSO (1 mL) were injected into the flask under argon atmosphere. The contents were then stirred at 80 °C for 24 h. After allowing the mixture to cool to r.t., the mixture was diluted with EtOAc (20 mL) and filtered. The filtrate was washed with H₂O (2 × 10 mL). The organic phase was dried with Na₂SO₄, filtered, and the solvent was removed under vacuum, and the residue was purified by chromatography on silica gel to give the desired aryl sulfide. Spectroscopic Data of the Representative Compounds: (2,4,6-Trimethylphenyl)phenyl Sulfide (3c) ¹HNMR (400 MHz, CDCl₃): δ = 7.19–7.15 (t, J = 7.60 Hz, 2 H), 7.07–7.01 (m, 3 H), 6.93–6.91 (d, J = 7.60 Hz, 2 H), 2.39 (s, 6 H), 2.32 (s, 3 H). ¹³C NMR (125 MHz, CDCl₃): δ = 143.7, 139.2, 138.4, 129.3, 128.8, 126.9, 125.5, 124.4, 21.7, 21.1. 3-Pyridyl Phenyl Sulfide (3m) ¹HNMR (400 MHz, CDCl₃): δ = 8.56–8.55 (s, 1 H), 8.46–8.45 (q, J = 4.8 Hz, 1 H), 7.60–7.58 (d, J = 8.00 Hz, 1 H), 7.39–7.29 (m, 5 H), 7.22–7.19 (q, J = 4.80 Hz, 1 H). ¹³C NMR (125 MHz, CDCl₃): δ = 151.1, 147.8, 137.9, 133.9, 133.6, 131.7, 129.5, 127.8, 123.9. 2-(4-Tolylsulfanyl)phenyl Bromide (3o) ¹HNMR (400 MHz, CDCl₃): δ = 7.54–7.52 (d, J = 7.6 Hz, 1 H), 7.40–7.38 (d, J = 8.00 Hz, 2 H), 7.23–7.21 (d, J = 8.00 Hz, 1 H), 7.13–7.08 (m, 1 H), 7.00–6.96 (m, 1 H), 6.82–6.79 (dd, J = 7.60 Hz, 1 H), 2.38 (s, 3 H). ¹³C NMR (125 MHz, CDCl₃): δ = 139.8, 139.0, 134.4, 132.9, 130.5, 128.7, 128.7, 127.7, 126.6, 122.0, 21.3.

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