Electron-Deficient Alloxazinium Salts: Efficient Organocatalysts of Mild and Chemoselective Sulfoxidations with Hydrogen Peroxide

Result code in IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61388955%3A_____%2F13%3A00399703" target="_blank" >RIV/61388955:_____/13:00399703 - isvavai.cz</a>

Alternative codes found

RIV/60461373:22310/13:43896597 RIV/60461373:22810/13:43896597

Result on the web

<a href="http://dx.doi.org/10.1002/adsc.201300617" target="_blank" >http://dx.doi.org/10.1002/adsc.201300617</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1002/adsc.201300617" target="_blank" >10.1002/adsc.201300617</a>

Result language

angličtina

Original language name

Electron-Deficient Alloxazinium Salts: Efficient Organocatalysts of Mild and Chemoselective Sulfoxidations with Hydrogen Peroxide

Original language description

A series of substituted alloxazinium perchlorates has been prepared and tested as catalysts for the oxidation of sulfides to sulfoxides with hydrogen peroxide. The logarithms of the observed rate constants of thioanisole oxidation correlate with the Hammett ? constants of the substituents on the alloxazinium catalysts, as well as with their reduction potentials E0 and their pKR+ values, representing the alloxazinium salt/pseudobase equilibrium. The stronger the electron-withdrawing substituent, the moreefficient is the alloxazinium catalyst. The alloxazinium salts with a cyano or trifluoromethyl group in position 8 proved to be the most efficient, operating at room temperature at small loadings, down to 0.1?mol%, achieving turnover number values of upto 640 and acceleration by a factor of 350 relative to the non-catalyzed oxidation. The 8-cyanoalloxazinium perchlorate was evaluated as the best catalyst; however, due to its relatively good accessibility, the 8-(trifluoromethyl)alloxaz

Czech name

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Czech description

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Type

J_x - Unclassified - Peer-reviewed scientific article (Jimp, Jsc and Jost)

CEP classification

CF - Physical chemistry and theoretical chemistry

OECD FORD branch

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Project

<a href="/en/project/GAP207%2F12%2F0447" target="_blank" >GAP207/12/0447: Organocatalytic stereoselective oxidations using heterocyclic hydroperoxides</a><br>

Continuities

I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Publication year

2013

Confidentiality

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Name of the periodical

Advanced Synthesis & Catalysis

ISSN

1615-4150

e-ISSN

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Volume of the periodical

355

Issue of the periodical within the volume

17

Country of publishing house

DE - GERMANY

Number of pages

12

Pages from-to

3451-3462

UT code for WoS article

000327984000020

EID of the result in the Scopus database

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