Selective sulfoxidation of thioethers and thioaryl boranes with nitrate, promoted by a molybdenum-copper catalytic system

Journal of Organic Chemistry

Volumn 76, Issue 13, 2011, Pages 5240-5246

  Marom, Hanit ^a   Antonov, Svetlana ^a   Popowski, Yanay ^a   Gozin, Michael ^a  

^a TEL AVIV UNIVERSITY   (Israel)

Author keywords

[No Author keywords available]

Indexed keywords

BORONIC ACID; BORONIC ESTERS; CATALYTIC PROCESS; CATALYTIC REACTIONS; CATALYTIC REDUCTION; CATALYTIC SYSTEM; CHEMICAL TRANSFORMATIONS; CHEMOSELECTIVE; COMPLEX 1; NITRATE SALTS; NMR TECHNIQUES; ORGANOBORON COMPOUND; REACTION CONDITIONS; REACTION MECHANISM; SODIUM NITRATES; SULFOXIDATION; SUZUKI CROSS COUPLING; SYNTHETIC ORGANIC CHEMISTRY; THIOETHERS;

ACETONITRILE; BORON COMPOUNDS; CATALYSIS; CATALYSTS; CHLORINE; CHLORINE COMPOUNDS; FUNCTIONAL GROUPS; MOLYBDENUM; MOLYBDENUM OXIDE; NITRATES; OXIDANTS;

SELECTIVE CATALYTIC REDUCTION;

BORANE DERIVATIVE; BORONIC ACID DERIVATIVE; COPPER; COPPER DERIVATIVE; ESTER; FUNCTIONAL GROUP; MOLYBDENUM; MOLYBDENUM COMPLEX; NITRATE; NITRITE; NITROGEN; ORGANOBORON DERIVATIVE; OXIDIZING AGENT; OXYGEN 18; SODIUM NITRATE; SULFIDE; THIOESTER;

ARTICLE; CATALYSIS; CATALYST; CONTROLLED STUDY; NITROGEN NUCLEAR MAGNETIC RESONANCE; ORGANIC CHEMISTRY; PHOSPHORUS NUCLEAR MAGNETIC RESONANCE; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; REDUCTION; STEREOCHEMISTRY; SULFOXIDATION; SUZUKI REACTION;

BORANES; CATALYSIS; COPPER; CRYSTALLOGRAPHY, X-RAY; MODELS, MOLECULAR; MOLECULAR STRUCTURE; MOLYBDENUM; NITRATES; ORGANOMETALLIC COMPOUNDS; OXIDATION-REDUCTION; SAFROLE; SULFIDES;

EID: 79959671696     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo2001808     Document Type: Article

References (55)

1. Lane, B. S.; Burgess, K. Chem. Rev. 2003, 103, 2457-2473
2. Nugent, W. A.; RajanBabu, T. V.; Burk, M. J. Science 1993, 259, 479-483
3. Veiros, L. F.; Prazeres, Â.; Costa, P. J.; Romão, C. C.; Kühn, F. E.; Calhorda, M. J. Dalton Trans. 2006, 11, 1383-1389
4. Güenyar, A.; Betz, D.; Drees, M.; Herdtweck, E.; Kühn, F. E. J. Mol. Catal. A: Chem. 2010, 331, 117-124
5. Coughlan, M. P. Molybdenum and Molybdenum-Containing Enzymes; Pergamon Press: New York, 1980.
6. Spiro, T. G. Molybdenum Enzymes; Wiley-Interscience: New York, 1985.
7. Hille, R. Chem. Rev. 1996, 96, 2757-2816
8. Romao, M. J. Structure 1999, 7, 65-79
9. Güenter, S.; Mendel, R. R.; Ribbe, M. W. Nature 2009, 460, 839-847
10. Holm, R. H. Chem. Rev. 1987, 87, 1401-1449
11. Nagarajan, K.; Joshi, H. K.; Chaudhury, K.; Pal, K.; Cooney, J. J. A.; Enemark, J. H.; Sarkar, S. Inorg. Chem. 2004, 43, 4532-4533
12. Enemark, J. H.; Cooney, J. J. A.; Wang, J.; Holm, R. H. Chem. Rev. 2004, 104, 1175-1200
13. Kail, B. W.; Perez, L. M.; Zaric, S. D.; Millar, A. J.; Young, C. G.; Hall, M. B.; Basu, P. Chem.-Eur. J. 2006, 12, 7501-7509
14. Smith, P. D.; Millar, A. J.; Young, C. G.; Ghosh, A.; Basu, P. J. Am. Chem. Soc. 2000, 122, 9298-9299
15. Nemykin, V. N.; Laskin, J.; Basu, P. J. Am. Chem. Soc. 2004, 126, 8604-8605
16. Millar, A. J.; Doonan, C. J.; Smith, P. D.; Nemykin, V. N.; Basu, P.; Young, C. G. Chem.-Eur. J. 2005, 11, 3255-3267
17. Sengar, R. S.; Nemykin, V. N.; Basu, P. J. Inorg. Biochem. 2008, 102, 748-756
18. Gasparrini, F.; Giovannoli, M.; Misiti, D.; Natile, G.; Palmieri, G. Tetrahedron 1983, 39, 3181-3184
19. Yuan, Y.; Bian., Y. Tetrahedron Lett. 2007, 48, 8518-8520
20. Komatsu, N.; Uda, M.; Suzuki, H. Chem. Lett. 1997, 1229-1230
21. Komatsu, N.; Taniguchi, A.; Wada, S.; Suzuki, H. Adv. Synth. Catal. 2001, 343, 473-480
22. Holland, H. L. Chem. Rev. 1988, 88, 473-485
23. Block, E. Angew. Chem., Int. Ed. Engl. 1992, 31, 1135-1178
24. Jones, C. W. Application of Hydrogen Peroxide and Derivatives; MPG Books Ltd.: Cornwall, UK, 1999.
25. Adam, W. Peroxide Chemistry Mechanistic and Preparative Aspects of Oxygen Transfer; Wiley-VCH: Darmstadt, Germany, 2000.
26. Hudlicky, M. ACS Monogr. 1990, 433
27. Procter, D. J. J. Chem. Soc., Perkin Trans. 1 1999, 641-668
28. Mata, E. G. Phosphorus, Sulfur Silicon Relat. Elem. 1996, 117, 231-286
29. Madesclaire, M. Tetrahedron 1986, 42, 5459-5495
30. Caron, S.; Dugger, R. W.; Ruggeri, S. G.; Ragan, J. A.; Ripin, D. H. Chem. Rev. 2006, 106, 2943-2989
31. Sato, K.; Hyodo, M.; Aoki, M.; Zheng, X.-Q.; Noyori, R. Tetrahedron 2001, 57, 2469-2476
32. Fraile, J. M.; Lazaro, B.; Mayoral, J. A. Chem. Commun. 1998, 1807-1808
33. Thiel, W. R.; Barz, M.; Glas, H.; Pleier, A. K. Peroxide Chem. 2000, 433-453
34. Sharpless, K. B.; Townsend, J. M.; Williams, D. R. J. Am. Chem. Soc. 1972, 94, 295-296
35. Lane, B. S.; Burgess, K. Chem. Rev. 2003, 103, 2457-2473
36. Gago, S.; Neves, P.; Monteiro, B.; Pessêgo, M.; Lopes, A. D.; Valente, A. A.; Almeida Paz, F. A.; Pillinger, M.; Moreira, J.; Silva, C. M.; Goncalves, I. S. Eur. J. Inorg. Chem. 2009, 4528-4537
37. Veiros, L. F.; Prazeres, A.; Costa, P. J.; Romão, C. C.; Kühn, F. E.; Calhorda, M. J. Dalton Trans. 2006, 1383-1389
38. Groarke, M.; Goncalves, I. S.; Herrmann, W. A.; Kühn, F. E. J. Organomet. Chem. 2002, 649, 108-112
39. Kühn, F. E.; Santos, A. G.; Lopes, A. D.; Goncalves, I. S.; Rodríguez-Borges, J. E.; Pillinger, M.; Romão, C. C. J. Organomet. Chem. 2001, 621, 207-217
40. Butcher, R. J.; Penfold, B. R.; Sinn, E. J. Chem. Soc., Dalton Trans. 1979, 4, 668-675
41. Wang, G.; Chen, G.; Luck, R. L.; Wang, Z.; Mu, Z.; Evans, D. G.; Duan, X. Inorg. Chim. Acta 2004, 357, 3223-3229
42. Chatt, J.; Elson, C. M.; Leigh, G. J.; Connor, J. A. J. Chem. Soc., Dalton Trans. 1976, 14, 1351-1354
43. Klein, R.; Friedel, R. A. J. Am. Chem. Soc. 1950, 72, 3810-3811
44. Kool, D. M.; Wrage, N.; Oenema, O.; Dolfing, J.; Van Groenigen, J. W. Rapid Commun. Mass Spectrom. 2007, 21, 3569-3578
45. Kinen, C. O.; Rossi, L. I.; De Rossi, R. H. J. Org. Chem. 2009, 74, 7132-7139
46. Hille, R. Chem. Rev. 1996, 96, 2757-2816
47. Holm, R. H. Coord. Chem. Rev. 1990, 100, 183-221
48. Amirav, A.; Gordin, A.; Poliak, M.; Fialkov, A. B. J. Mass. Spectrom 2008, 43, 141-163
49. Ali, M. H. Synthesis 2007, 3507-3511
50. Caupene, C. J. Org. Chem. 2005, 70, 2812-2815
51. Foucoin, F. Synthesis 2007, 1315-1324
52. Gao, Y. Adv. Synth. Catal. 2008, 350, 2937-2946
53. Claudel, S.; Gosmini, C.; Paris, J. M.; Périchon, J. Chem. Commun. 2007, 35, 3667-3669
54. Spencer, J. ACS Comb. Sci. 2011, 13, 24-31
55. Claudel, S. Chem. Commun. 2007, 3667-3669