Electron-Deficient Heteroarenium Salts: An Organocatalytic Tool for Activation of Hydrogen Peroxide in Oxidations

Result code in IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F60461373%3A22310%2F15%3A43900223" target="_blank" >RIV/60461373:22310/15:43900223 - isvavai.cz</a>

Alternative codes found

RIV/60461373:22810/15:43900223

Result on the web

<a href="http://pubs.acs.org/doi/full/10.1021/jo502865f" target="_blank" >http://pubs.acs.org/doi/full/10.1021/jo502865f</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1021/jo502865f" target="_blank" >10.1021/jo502865f</a>

Result language

angličtina

Original language name

Electron-Deficient Heteroarenium Salts: An Organocatalytic Tool for Activation of Hydrogen Peroxide in Oxidations

Original language description

A series of monosubstituted pyrimidinium and pyrazinium triflates and 3,5-disubstituted pyridinium triflates were prepared and tested as simple catalysts of oxidations with hydrogen peroxide, using sulfoxidation as a model reaction. Their catalytic efficiency strongly depends on the type of substituent and is remarkable for derivatives with an electron-withdrawing group, showing reactivity comparable to that of flavinium salts which are the prominent organocatalysts for oxygenations. Because of their high stability and good accessibility, 4-(trifluoromethyl)pyrimidinium and 3,5-dinitropyridinium triflates are the catalysts of choice and were shown to catalyze oxidation of aliphatic and aromatic sulfides to sulfoxides, giving quantitative conversions, high preparative yields and excellent chemoselectivity. The high efficiency of electron-poor heteroarenium salts is rationalized by their ability to readily form adducts with nucleophiles, as documented by low pKR+ values (pKR+ < 5) and le

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

CA - Inorganic 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

S - Specificky vyzkum na vysokych skolach

Publication year

2015

Confidentiality

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

Name of the periodical

Journal of Organic Chemistry

ISSN

0022-3263

e-ISSN

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Volume of the periodical

80

Issue of the periodical within the volume

5

Country of publishing house

US - UNITED STATES

Number of pages

24

Pages from-to

2676-2699

UT code for WoS article

000350841600022

EID of the result in the Scopus database

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