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Synlett 2012; 23(19): 2853-2857
DOI: 10.1055/s-0032-1317518
DOI: 10.1055/s-0032-1317518
letter
8-Hydroxyquinolin-N-oxide-Promoted Copper-Catalyzed C–S Cross-Coupling of Thiols with Aryl Iodides
Weitere Informationen
Publikationsverlauf
Received: 27. August 2012
Accepted after revision: 10. Oktober 2012
Publikationsdatum:
13. November 2012 (online)
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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 reactionSupporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synlett.
- Supporting Information
-
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.
For recent contributions on Pd-catalyzed C–S coupling reactions, see:
For recent contributions on Cu-catalyzed C–S coupling reactions, see:
For recent contributions on Ni-catalyzed C–S coupling reactions, see:
For recent contributions on Fe-catalyzed C–S coupling reactions, see:
For recent contributions on In-catalyzed C–S coupling reactions, see: