Mild hydrosulfenylation of Olefins under neutral conditions using a defined NHC-ligated iron-sulfur catalyst

ACS Catalysis

Volumn 3, Issue 12, 2013, Pages 3002-3005

  Alt, Isabel ^a   Rohse, Philipp ^a   Plietker, Bernd ^a  

^a UNIVERSITY OF STUTTGART   (Germany)

Author keywords

addition; carbene ligand; catalysis; iron; sulfur

Indexed keywords

ADDITION; CARBENE LIGANDS; CATALYST LOADINGS; EFFICIENT CATALYSTS; EQUIMOLAR AMOUNT; MILD REACTION CONDITIONS; NEUTRAL CONDITIONS; UNSATURATED KETONES;

CATALYSIS; CATALYSTS; IRON; KETONES; LIGANDS; SULFUR;

IRON COMPOUNDS;

EID: 84890391015     PISSN: 21555435     EISSN: None     Source Type: Journal    
DOI: 10.1021/cs4009336     Document Type: Article

References (35)

1. Hegedus, L. L.; McCabe, R. W. Catalyst Poisoning; Marcel Dekker: New York, 1984.
2. Hutton, A. T. In Comprehensive Coordination Chemistry; Wilkinson, G., Gillard, R. D., McCleverty, J. A., Eds.; Pergamon Press: Oxford, UK, 1984, Vol 5, p 1151.
3. Iron: (i) Correa, A.; Carril, M.; Bolm, C. Angew. Chem., Int. Ed. 2008, 47, 2880-2883
4. Wu, J.-R.; Lin, C.-H.; Lee, C.-F. Chem. Commun. 2009, 4450-4452
5. Silica: Chen, C.-K.; Chen, Y.-W.; Lin, C.-H.; Lin, H.-P.; Lee, C.-F. Chem. Commun. 2010, 46, 282-284
6. Palladium: Fernández-Rodríguez, M. A.; Shen, Q.; Hartwig, J. F. J. Am. Chem. Soc. 2006, 128, 2180-2181
7. Iridium: Zheng, S.; Gao, N.; Liu, W.; Liu, D.; Zhao, X.; Cohen, T. Org. Lett. 2010, 12, 4454
8. Palladium: (i) Goux, C.; Lohste, P.; Sinou, D. Tetrahedron Lett. 1992, 33, 8099
9. Goux, C.; Lohste, P.; Sinou, D. Tetrahedron Lett. 1994, 34, 10321
10. Frank, M.; Gais, H.-J. Tetrahedron: Asymmetry 1998, 9, 3353
11. Gais, H.-J.; Jagusch, T.; Spalthoff, N.; Gerhards, F.; Frank, M.; Raabe, G. Chem.-Eur. J. 2003, 9, 4202
12. Ruthenium: Zaitsev, A. B.; Caldwell, H. F.; Pregosin, P. S.; Veiros, L. F. Chem.-Eur. J. 2009, 15, 6468
13. Iron: Lin, Y.-Y.; Wang, Y.-J.; Lin, C.-H.; Cheng, J.-H.; Lee, C.-F. J. Org. Chem. 2012, 77, 6100-6106
14. Gao, N.; Zheng, S.; Yang, W.; Zhao, X. Org. Lett. 2011, 13, 1514
15. A review is found in Liu, W.; Zhao, Y. Synthesis 2013, 2051
16. C,S bond formation in biological systems: Fontecave, M.; Ollagnier-De-Choudens, S.; Mulliez, E. Chem. Rev. 2003, 103, 2149
17. "Click"-type chemistry using thiols: Hoyle, C. E.; Lowe, A. B.; Bowman, C. N. Chem. Soc. Rev. 2010, 39, 1355
18. Science of Synthesis: Category 5, Compounds with One Saturated Carbon Heteroatom Bond. Sulfur, Selenium, and Tellurium; Kambe, N.,; Aleman, J., Eds.; Thieme-Verlag: Stuttgart, Germany, 2008.
19. Metal-catalyzed C,S bond formations: Kondo, T.; Mitsudo, T. Chem. Rev. 2000, 100, 3205
20. Copper: Garg, S. K.; Kumar, R.; Chakraborti, A. K. Tetrahedron Lett. 2005, 46, 1721-1724
21. Nickel: Kanemasa, S.; Oderaotoshi, Y.; Wada, E. J. Am. Chem. Soc. 1999, 121, 8675-8676
22. For a review on sulfa-Michael additions, see: Enders, D.; Lüttgen, K.; Narine, A. A. Synthesis 2007, 959 see also refs 2 and 3
23. Delp, S. A.; Munro-Leighton, C.; Goj, L. A.; Ramírez, M. A.; Gunnoe, T. B.; Petersen, J. L.; Boyle, P. D. Inorg. Chem. 2007, 46, 2365-2367
24. Hsieh, C.-H.; Darensbourg, M. Y. J. Am. Chem. Soc. 2010, 132, 14118-14125
25. Pulukkody, R.; Kyran, S. J.; Bethel, R. D.; Hsieh, C.-H.; Hall, M. B.; Darensbourg, D. J.; Darensbourg, M. Y. J. Am. Chem. Soc. 2013, 135, 8423-8430
26. Holzwarth, M. S.; Frey, W.; Plietker, B. Chem. Commun. 2011, 47, 11113-11115
27. Iron Catalysis: Fundamentals and Applications: 33 (Topics in Organometallic Chemistry); Plietker, B., Ed.; Springer: Berlin, 2010, Vol. 1.
28. Iron Catalysis in Organic Chemistry: Reactions and Applications; Plietker, B., Ed.; Wiley-VCH: Weinheim, 2008, Vol. 1. For selected reviews on iron catalysis,see
29. Bolm, C.; Legros, J.; Le Paih, J.; Zani, L. Chem. Rev. 2004, 104, 6217-6254
30. Correa, A.; Mancheno, O. G.; Bolm, C. Chem. Soc. Rev. 2008, 37, 1108-1117
31. Czaplik, W. M.; Mayer, M.; Cvengros, J.; Jacobi von Wangelin, A. ChemSusChem 2009, 38, 396-417
32. Morris, R. H. Chem. Soc. Rev. 2009, 38, 2282-2291
33. Darwish, M.; Wills, M. Catal. Sci. Technol. 2012, 2, 243-255
34. Sherry, B. D.; Fürstner, A. Acc. Chem. Res. 2008, 41, 1500-1511
35. Yamada, H.; Kinoshita, H.; Inomata, K.; Kotake, H. Bull. Chem. Soc. Jpn. 1983, 56, 949-950