Rapid and mild deoxygenation of sulfoxides with MoCl5/gallium system under ultrasonication

Bulletin of the Korean Chemical Society

Volumn 30, Issue 9, 2009, Pages 1927-1928

  Yoo, Byung Woo ^a   Park, Min Chol ^a   Shin, Jae In ^a  

^a Korea University   (South Korea)

Author keywords

Deoxygenation; Gallium; Molybdenum; Sulfoxides

Indexed keywords

EID: 75649112983     PISSN: 02532964     EISSN: 12295949     Source Type: Journal    
DOI: 10.5012/bkcs.2009.30.9.1927     Document Type: Article

References (27)

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24. A typical procedure for the deoxygenation of sulfoxides is as follows: To a solution of molybdenum pentachloride (238 mg, 1.0 mmol), diphenylsulfoxide (101 mg, 0.5 mmol) in anhydrous THF (5 mL) were added gallium (230 mg, 2.0 mmol). The resulting mixture was stirred at room temperature under sonication and the progress of the reaction was followed by TLC. After completion of the reaction (10 min) the reaction was quenched with aq. NaOH (10%), and extracted with ether. The combined ethereal extracts were washed successively with brine (20 mL) and H2O (20 mL). The organic layer was separated and dried over anhydrous Na2SO4. The ether was removed under reduced pressure and the obtained crude product was purified by silica gel column chromatography (hexane:ethyl acetate=2:1) to afford diphenylsulfide (86 mg, 92%). Selected spectral data: Diphenylsulfide (entry 1): 1H NMR (300 MHz, CDCl3) ( 7.38 - 7.25 (m, 10H). 13C NMR (75 MHz, CDCl3) ( 135.7, 131.1, 129.2, 127.1. Di(p-anisole) sulfide (entry 5): 1H NMR (300 MHz, CDCl3) ( 6.84 - 7.28 (m, 8H), 3.79 (s, 3H). 13C NMR (75 MHz, CDCl3) ( 162.2, 137.4, 127.3, 115.1, 55.9. Methyl p-tolyl sulfide (entry 8): 1H NMR (300 MHz, CDCl3) ( 7.54 (d, 2H, J=11.1 Hz), 7.33 (d, 2H, J=8.1 Hz), 2.70 (s, 3H), 2.41 (s, 3H). 13C NMR (75 MHz, CDCl3) ( 134.9, 134.6, 129.6, 127.4, 20.9, 16.6. Benzyl phenyl sulfide (entry 11): 1H NMR (300 MHz, CDCl3) ( 7.33 - 7.19 (m, 10H), 4.13 (s, 2H). 13C NMR (75 MHz, CDCl3) ( 137.4, 136.3, 129.9, 128.8, 128.5, 127.5, 127.1, 126.4, 39.2. Dibutylsulfide (entry 12): 1H NMR (300 MHz, CDCl3) ( 2.65 (t, 4H, J=7.2 Hz), 1.71 (m, 4H), 1,55 (m, 4H), 1.04 (t, 6H, J=7.2 Hz). 13C NMR (75 MHz, CDCl3) ( 32.0, 30.3, 22.2, 13.8.
25. Sonication were carried out in BRANSONIC ultrasonic cleaner bath, which delievered a 47 kHz wave, with a fixed electrical power of 125 Watts.
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