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Original Articles

Copper-catalyzed cross-coupling reaction of thiols with aryl halides

Pages 678-681 | Received 28 Mar 2019, Accepted 01 Apr 2019, Published online: 20 Apr 2019

References

  • Lee, C.-F; Basha, R. S.; Badsara, S. S. Engineered C-S Bond Construction. Top. Curr. Chem 2018, 376, 25.
  • (a) Kondo, T.; Mitsudo, T. A. Metal-Catalyzed Carbon-Sulfur Bond Formation. Chem. Rev. 2000, 100, 3205–3220. (b) Beletskaya, I. P.; Ananikov, V. P. Transition-Metal-Catalyzed C − S, C − Se, and C − Te Bond Formation via Cross-Coupling and Atom-Economic Addition Reactions. Chem. Rev. 2011, 111, 1596–1636. (c) Liu, H.; Jiang, X. Heteroacene Synthesis through C − S Cross‐Coupling/5-endo-dig Cyclization. Chem. Asian J. 2013, 8, 2546–2563. (d) Lee, C.-F.; Liu, Y.-C.; Badsara, S. S. Transition-Metal-Catalyzed C-S Bond Coupling Reaction. Chem. Asian J. 2014, 9, 706–722.
  • Alcaraz, M.-L.; Atkinson, S.; Cornwall, P.; Foster, A. C.; Gill, D. M.; Humphries, L. A.; Keegan, P. S.; Kemp, R.; Merifield, E.; Nixon, R. A.; et al. Efficient Syntheses of AZD4407 via Thioether Formation by Nucleophilic Attack of Organometallic Species on Sulphur. Org. Process Res. Dev. 2005, 9, 555–569. DOI: 10.1021/op0500483.
  • Sheehan, J. C.; Henery-Logan, K. R. The Total Synthesis of Penicillin V. J. Am. Chem. Soc. 1959, 81, 3089–3094. DOI: 10.1021/ja01521a044.
  • Raghavan, S.; Krishnaiah, V.; Sridhar, B. Asymmetric Synthesis of the Potent HIV-Protease Inhibitor, Nelfinavir. J. Org. Chem. 2010, 75, 498–501. DOI: 10.1021/jo902048t.
  • Braun, A.; Zhang, S.; Miettinen, H. E.; Ebrahim, S.; Holm, T. M.; Vasile, E.; Post, M. J.; Yoerger, D. M.; Picard, M. H.; Krieger, J. L.; et al. Probucol Prevents Early Coronary Heart Disease and Death in the High-Density Lipoprotein Receptor SR-BI/Apolipoprotein E Double Knockout Mouse. Proc. Natl. Acad. Sci. USA. 2003, 100, 7283–7288. DOI: 10.1073/pnas.1237725100.
  • Kosugi, M.; Shimizu, T.; Migita, T. Reactions of Aryl Halides with Thiolate Anions in the Presence of Catalytic Amounts of Tetrakis(Triphenylphosphine)Palladium Preparation of Aryl Sulfides. Chem. Lett. 1978, 7, 13–14. DOI: 10.1246/cl.1978.13.
  • Fernández-Rodríguez, M. A.; Shen, Q.; Hartwig, J. F. A General and Long-Lived Catalyst for the Palladium-Catalyzed Coupling of Aryl Halides with Thiols. J. Am. Chem. Soc. 2006, 128, 2180–2181. DOI: 10.1021/ja0580340.
  • Fernández-Rodríguez, M. A.; Hartwig, J. F. One-Pot Synthesis of Unsymmetrical Diaryl Thioethers by Palladium-Catalyzed Coupling of Two Aryl Bromides and a Thiol Surrogate. Chemistry 2010, 16, 2355–2359. DOI: 10.1002/chem.200902313.
  • Kwong, F. Y.; Buchwald, S. L. A General, Efficient, and Inexpensive Catalyst System for the Coupling of Aryl Iodides and Thiols. Org. Lett. 2002, 4, 3517–3520.
  • Chen, Y.-J.; Chen, H.-H. 1,1,1-tris(Hydroxymethyl)Ethane as a New, Efficient, and Versatile Tripod Ligand for Copper-Catalyzed Cross-Coupling Reactions of Aryl Iodides with Amides, Thiols, and Phenols. Org. Lett. 2006, 8, 5609–5612. DOI: 10.1021/ol062339h.
  • Kao, H.-L.; Lee, C.-F. Efficient Copper-Catalyzed S-Vinylation of Thiols with Vinyl Halides. Org. Lett. 2011, 13, 5204–5207. DOI: 10.1021/ol2020863.
  • Chen, C.-K.; Chen, Y.-W.; Lin, C.-H.; Lin, H.-P.; Lee, C.-F. Synthesis of CuO on Mesoporous Silica and Its Applications for Coupling Reactions of Thiols with Aryl Iodides. Chem. Commun. (Camb.) 2010, 46, 282–284. DOI: 10.1039/b918117b.
  • Cheng, J.-H.; Yi, C.-L.; Liu, T.-J.; Lee, C.-F. Highly Regioselective Synthesis of Aryl Chalcogenides through C-H Functionalization of Arenes. Chem. Commun. (Camb.) 2012, 48, 8440–8442. DOI: 10.1039/c2cc33950a.
  • Hsu, W.-C.; Li, C.-E.; Lee, C.-F. Para -Selective C − H Thioetherification. Asian J. Org. Chem. 2017, 6, 1667–1673. DOI: 10.1002/ajoc.201700336.
  • Chen, C.-W.; Chen, Y.-L.; Reddy, D. M.; Du, K.; Li, C.-E.; Shih, B.-H.; Xue, Y.-J.; Lee, C.-F. CuI/Oxalic Diamide-Catalyzed Cross-Coupling of Thiols with Aryl Bromides and Chlorides. Chemistry 2017, 23, 10087–10091. DOI: 10.1002/chem.201701671.

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