Efficient metal-free aerobic photooxidation of sulfides to sulfoxides mediated by a vitamin B2 derivative and visible light
The result's identifiers
Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F60461373%3A22810%2F16%3A43902793" target="_blank" >RIV/60461373:22810/16:43902793 - isvavai.cz</a>
Alternative codes found
RIV/60461373:22310/16:43902793
Result on the web
<a href="http://dx.doi.org/10.1002/adsc.201501123" target="_blank" >http://dx.doi.org/10.1002/adsc.201501123</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1002/adsc.201501123" target="_blank" >10.1002/adsc.201501123</a>
Alternative languages
Result language
angličtina
Original language name
Efficient metal-free aerobic photooxidation of sulfides to sulfoxides mediated by a vitamin B2 derivative and visible light
Original language description
We developed a metal-free process for the aerobic photooxygenation of sulfides to sulfoxides mediated by riboflavin tetraacetate or riboflavin (vitamin B2) photocatalysts and visible light (455 nm) in acetonitrile-water (85:15 v/v) mixture. The optimised solvent system leads to both singlet-oxygen and electron-transfer pathways in photooxygenation, thus allowing oxidation of electron-poor and electron-rich thioanisoles, dialkyl sulfides and sterically hindered sulfides. Besides having a broad substrate scope, the method has very short reaction times and requires low catalyst loading (down to 0.1 mol%). These properties are due to the high photocatalyst stability and the extremely high quantum yields (1.3 for thioanisole oxygenation). Moreover, the method is chemoselective, producing only sulfoxides without over-oxidation to sulfones. Taking into account broad substrate scope, high selectivity and high efficiency, this method distinguishes itself from those previously reported. Other advantages include easy work-up of the reaction mixture, the availability and biodegradability of the photocatalysts and mild reaction conditions. We demonstrated, on a preparative scale, its practical application in the synthesis of the psychostimulant modafinil, in the selective oxidation of methionine derivatives, and in the detoxification of mustard gas.
Czech name
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Czech description
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Classification
Type
J<sub>x</sub> - Unclassified - Peer-reviewed scientific article (Jimp, Jsc and Jost)
CEP classification
CC - Organic chemistry
OECD FORD branch
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Result continuities
Project
<a href="/en/project/GA14-09190S" target="_blank" >GA14-09190S: Towards photoorganocatalytic metathesis: [2+2] cycloaddition of alkenes and cyclobutane ring cleavage mediated by flavins and visible light</a><br>
Continuities
P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)
Others
Publication year
2016
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Data specific for result type
Name of the periodical
ADVANCED SYNTHESIS & CATALYSIS
ISSN
1615-4150
e-ISSN
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Volume of the periodical
358
Issue of the periodical within the volume
10
Country of publishing house
DE - GERMANY
Number of pages
10
Pages from-to
"1654?1663"
UT code for WoS article
000377268100015
EID of the result in the Scopus database
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