2021
DOI: 10.1039/d1ob01632f
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Selective synthesis of sulfoxides and sulfones via controllable oxidation of sulfides with N-fluorobenzenesulfonimide

Abstract: A practical and mild method for the switchable synthesis of sulfoxides or sulfones via selective oxidation of sulfides using cheap N-fluorobenzenesulfonimide (NFSI) as oxidant has been developed. These highly chemoselective...

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Cited by 20 publications
(13 citation statements)
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“…13 C­{ 1 H} NMR (101 MHz, DMSO- d ) δ 161.7, 132.0, 129.3, 115.9. All spectral data match those previously reported …”
Section: Experimental Sectionsupporting
confidence: 86%
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“…13 C­{ 1 H} NMR (101 MHz, DMSO- d ) δ 161.7, 132.0, 129.3, 115.9. All spectral data match those previously reported …”
Section: Experimental Sectionsupporting
confidence: 86%
“…All spectral data match those previously reported. 27 Synthesis of 2-Hydroxypyridine (14). Following the general procedure, the crude product was purified using silica gel column chromatography (DCM−MeOH = 20:1) to produce the desired product 14; 14 was isolated as a brown solid (100 mg, 88% yield); 1 H NMR (400 MHz, DMSO-d) δ 11.59 (s, 1H), 7.46−7.32 (m, 2H), 6.31 (d, J = 9.2 Hz, 1H), 6.15 (td, J = 6.5, 0.8 Hz, 1H).…”
mentioning
confidence: 99%
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“…Likewise, we then applied this strategy in the synthesis of an acaricide chlorbenside ( 16 ), which could also be selectively converted into the sulfoxide derivative ( 18 ) by NFSI via a controllable oxidation. 28…”
Section: Resultsmentioning
confidence: 99%
“…Benzoxazoles 4a and 4b were synthesized to validate the utilization of our protocol. Another potent application is the synthesis of Dapsone 5 , a patented drug (trade name Aczone) for the treatment of leprosy (Scheme b).…”
mentioning
confidence: 99%