Pd-catalyzed reductive cleavage of alkyl aryl sulfides with triethylsilane that is accelerated by trialkylsilyl chloride

Tetrahedron Letters

Volumn 53, Issue 33, 2012, Pages 4313-4316

  Matsumura, Takehiko ^a   Niwa, Takashi ^a   Nakada, Masahisa ^a  

^a WASEDA UNIVERSITY   (Japan)

Author keywords

Alkyl aryl sulfide; Pd catalyzed; Reductive cleavage; Trialkylsilyl chloride; Triethylsilane

Indexed keywords

CHLORIDE; FUNCTIONAL GROUP; LIGAND; PALLADIUM; POLYCYCLIC AROMATIC HYDROCARBON; REAGENT; SILANE; SULFIDE; TRIALKYLSILYL CHLORIDE; TRIETHYLSILANE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL BOND; PROTON NUCLEAR MAGNETIC RESONANCE; REDUCTION; ROOM TEMPERATURE;

EID: 84864031108     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2012.06.002     Document Type: Article

References (40)

1. R. Mozingo, D.E. Wolf, S.A. Harris, and K. Folkers J. Am. Chem. Soc. 65 1943 1013 1016
2. G.A. Howard, B. Lythgoe, and A.R. Todd J. Chem. Soc. 1945 556 561
3. C.M. Shafer, and T.F. Molinski J. Org. Chem. 63 1998 551 555
4. 2: T. Sugimoto, N. Nishioka, S. Murata, and S. Matsuura Heterocycles 26 1987 2091 2092
5. Nickel boride: A. Zumbrunn Synthesis 1998 1357 1361
6. I. Kawasaki, N. Sakaguchi, A. Khadeer, M. Yamashita, and S. Ohta Tetrahedron 62 2006 10182 10192
7. Cobalt boride: T.G. Back, D.L. Baron, and K. Yang J. Org. Chem. 58 1993 2407 2413
8. Raney copper: W. Pfleiderer Tetrahedron 44 1988 3373 3378
9. NiCRA/NiCRAL: S. Becker, Y. Fort, R. Vanderesse, and P. Caubère J. Org. Chem. 54 1989 4848 4853
10. Trialkylstannanes: C.G. Gutierrez, R.A. Stringham, T. Nitasaka, and K.G. Glasscock J. Org. Chem. 45 1980 3393 3395
11. Zn/HCl: J.J. Baldwin, E.L. Engelhardt, R. Hirschmann, G.S. Ponticello, J.G. Atkinson, B.K. Wasson, C.S. Sweet, and A. Scriabine J. Med. Chem. 23 1980 65 70
12. 2O: C. Yamazaki, H. Arima, and S. Udagawa J. Heterocycl. Chem. 33 1996 41 44
13. Red-Al: T. Choshi, A. Tonari, H. Yoshioka, K. Harada, E. Sugino, and S. Hibino J. Org. Chem. 58 1993 7952 7954
14. H. Yoshioka, Y. Matsuya, T. Choshi, E. Sugino, and S. Hibino Chem. Pharm. Bull. 44 1996 709 714
15. Hydrazine-Pd/C: S. Niwas, P. Chand, V.P. Pathak, and J.A. Montgomery J. Med. Chem. 37 1994 2477 2480
16. H. Yamaguchi, and F. Ishikawa Chem. Pharm. Bull. 30 1982 326 332
17. Y. Ueno, A. Kojima, and M. Okawara Chem. Lett. 1984 2125 2128
18. A.M. Kawasaki, L.L. Wotring, and L.B. Townsend J. Med. Chem. 33 1990 3170 3176
19. S. Seto, and J. Asano Bioorg. Med. Chem. 15 2007 5083 5089
20. V. Kikelj, S. Grosjean, J.-C. Meslin, K. Julienne, and D. Deniaud Synthesis 2010 2811 2815
21. D.R. Williams, and L. Fu Synlett 2010 1641 1646
22. G. Rousseau, and B. Breit Angew. Chem., Int. Ed. 50 2011 2450 2494
23. N. Barbero, and R. Martin Org. Lett. 14 2012 796 799
24. T.H. Graham, W. Liu, and D.-M. Shen Org. Lett. 13 2011 6232 6235
25. R. Boukherroub, C. Chatgilialoglu, and G. Manuel Organometallics 15 1996 1508 1510
26. C. Ferreri, C. Costantino, C. Chatgilaloglu, R. Boukherroub, and G. Manuel J. Organomet. Chem. 554 1998 135 137
27. S. Vuoti, J. Autio, M. Laitila, M. Haukka, and J. Pursiainen Eur. J. Inorg. Chem. 2008 397 407
28. M. Mirza-Aghayan, R. Boukherroub, M. Rahimifard, and M. Bolourtchian Appl. Organomet. Chem. 24 2010 477 480
29. A. Kar, I.A. Sayyed, W.F. Lo, H.M. Kaiser, M. Beller, and M.K. Tse Org. Lett. 9 2007 3405 3408
30. F. Gelat, J. Jayashankaran, J.-F. Loheir, A.-C. Gaoumont, and S. Perrio Org. Lett. 13 2011 3170 3173
31. Z. Zhang, Z. Hu, Z. Yu, H. Chi, P. Lei, Y. Wang, and R. He Synth. Commun. 37 2007 683 690
32. I.C. González, L.N. Davis, and C.K. Smith II Bioorg. Med. Chem. Lett. 14 2004 4037 4043
33. G. Singh, H. Ila, and H. Junjappa Tetrahedron Lett. 25 1984 5095 5098
34. P. Gomes, C. Gosmini, J.-Y. Nédélec, and J. Périchon Tetrahedron Lett. 43 2002 5901 5903
35. C.V. Asokan, H. Ila, and H. Junjappa Synthesis 3 1987 284 285
36. T.R. Lee, and K. Kin J. Heterocycl. Chem. 26 1989 747 751
37. L. Bethge, D.V. Jarikote, and O. Seitz Bioorg. Med. Chem. 16 2008 114 125
38. R.A. Morton, and A.L. Stubbs J. Chem. Soc. 1939 1321 1324
39. J.Y. Corey, and J. Braddock-Wilking Chem. Rev. 99 1999 175 292
40. Y. Yamanoi J. Org. Chem. 70 2005 9607 9609 No silylated products were obtained in all the reactions reported here