Selective oxidation of sulfides to sulfoxides using a silica immobilised vanadyl alkyl phosphonate catalyst

Tetrahedron Letters

Volumn 47, Issue 46, 2006, Pages 8017-8019

  Al Hashimi, Mohammed ^a   Fisset, Emilie ^a   Sullivan, Alice C ^a   Wilson, John R H ^a  

^a QUEEN MARY UNIVERSITY OF LONDON   (United Kingdom)

Author keywords

Aqueous hydrogen peroxide; Immobilised reagents; Oxidation; Phosphonate; Silica; Sodium bromate; Sulfide; Sulfoxide; tert butyl hydroperoxide; Vanadyl

Indexed keywords

BROMATE; COBALT; HYDROGEN PEROXIDE; NICKEL; PHOSPHONIC ACID DERIVATIVE; SILICON DIOXIDE; SODIUM BROMATE; SULFIDE; SULFOXIDE; TERT BUTYL HYDROPEROXIDE; UNCLASSIFIED DRUG; VANADYL ALKYL PHOSPHONATE; VANADYL DERIVATIVE;

AQUEOUS SOLUTION; ARTICLE; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; OXIDATION; SYNTHESIS;

EID: 33749508651     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.09.065     Document Type: Article

References (19)

1. Sato K., Hyodo M., Aoki M., Zheng X.Q., and Noyori R. Tetrahedron 57 (2001) 2469-2476 See composite references 1 and 2 therein
2. Wang Y., Lente B., and Espenson J.H. Inorg. Chem. 41 (2002) 1272-1280
3. Reddy T.I., and Varma R.S. Chem. Commun. (1997) 471-472
4. Corma A., Iglesias M., and Sanchez F. Catal. Lett. 39 (1996) 153-156
5. Fraile M.J., Garcia J.I., Lazaro B., and Mayoral J.A. Chem. Commun. (1998) 1807-1808
6. Ayala V., Corma A., Iglesias M., and Sanchez F. J. Mol. Catal. A. 221 (2004) 201-208
7. Karimi B., Ghoreishi-Nezhad M., and Clark J.H. Org. Lett. 4 (2005) 625-628
8. Kantam M.L., Neelima B., Reddy Ch.V., Chaudhury M.K., and Dehury S.K. Catal. Lett. 95 (2004) 19-22
9. Maayan G., Popovitz-Biro R., and Neumann R. J. Am. Chem. Soc. 128 (2006) 4968-4969
10. Jurado-Gonzalez M., Sullivan A.C., and Wilson J.R.H. Tetrahedron Lett. 44 (2003) 4283-4286
11. Al-Haq N., Sullivan A.C., and Wilson J.R.H. Tetrahedron Lett. 44 (2003) 769-771
12. Jurado-Gonzalez M., Sullivan A.C., and Wilson J.R.H. J. Mater. Chem. 12 (2002) 3605-3609
13. Jurado-Gonzalez M., Sullivan A.C., and Wilson J.R.H. Tetrahedron Lett. 45 (2004) 4465-4468
14. Al-Hashimi M., Roy G., Sullivan A.C., and Wilson J.R.H. Tetrahedron Lett. 46 (2005) 4365-4368
15. -1) V 1.08, Co, 1.2 Ni, 1.3 was measured by determining the quantity of metal released from a known weight of material treated with conc. nitric acid using atomic absorption spectroscopy.
16. 3 system. The catalyst and sulfide (see Table 1 for quantities) were added to acetonitrile (3 mL) and then sodium bromate (0.23 g) and water (0.5 mL) were then added. This mixture was stirred at the temperature and for the time indicated in Table 1. The reaction was followed by TLC. The catalyst was separated by filtration and washed with ethyl acetate. The combined filtrate and ethyl acetate washings were then washed with water and the organic phase was separated and dried over magnesium sulfate. The product was obtained after removal of the solvent and the conversion was assessed by NMR.
17. 3 used (1.5 mmol) represents a large excess over that required to reoxidise the metal following the oxidation of 1 mmol of sulfide (assuming that sodium bromide is formed in the process).
18. 2 system. To a solution of sulfide in acetonitrile (5 mL) was added the catalyst followed either by a 70% aqueous solution of tert-butyl hydroperoxide or a 30% aqueous solution of hydrogen peroxide (see Table 1 for quantities). This reaction mixture was stirred at the temperature and for the time indicated and the progress of the reaction was monitored by TLC. After completion of the reaction, the catalyst was filtered and washed with diethyl ether. The combined organic fractions were washed with sodium sulfite (10% aq 10 mL), extracted with diethyl ether and the extract dried over magnesium sulfate. The solvent was evaporated to give the products and conversion was assessed without further purification by the inspection of the 270 MHz proton NMR spectra (account was taken of the relative integrations of resonances due to the sulfide, sulfoxide and sulfone as appropriate).
19. Filtrates taken after 30 min at the reaction temperature showed no further conversion up to 24 h.