Please use this identifier to cite or link to this item: http://dr.iiserpune.ac.in:8080/xmlui/handle/123456789/2208
Title: A Regioselective Synthesis of Benzopinacolones through Aerobic Dehydrogenative α‐Arylation of the Tertiary sp3 C-H Bond of 1,1‐Diphenylketones with Aromatic and Heteroaromatic Compounds
Authors: More, Nagnath Yadav
JEGANMOHAN, MASILAMANI
Dept. of Chemistry
Keywords: Regioselective Synthesis
Aerobic Dehydrogenative
Aromatic
Heteroaromatic Compounds
Aromatic and heteroaromatic
2015
Issue Date: Jan-2015
Publisher: Wiley
Citation: Chemistry - A European Journal, 21(3),1337-1342.
Abstract: A regioselective synthesis of symmetrical and unsymmetrical benzopinacolones through aerobic dehydrogenative α‐arylation at the tertiary sp3 CH bond of substituted 1,1‐diphenylketones with aromatic and heteroaromatic compounds, in the presence of K2S2O8 in CF3COOH at room temperature, is described. The reaction is proposed to go via a carbocation intermediate, which could be generated directly from cleavage of the sp3 CH bond of 1,1‐diphenylketone. Subsequent α‐arylation was achieved at the methene sp3 carbon atom of the substituted ketone. A variety of substituted aromatic and heteroaromatic compounds were compatible with this reaction. In addition, benzopinacolones were converted into sterically hindered, tetrasubstituted alkenes and polycyclic aromatic compounds.
URI: http://dr.iiserpune.ac.in:8080/xmlui/handle/123456789/2208
https://doi.org/10.1002/chem.201404308
ISSN: 0947-6539
1521-3765
Appears in Collections:JOURNAL ARTICLES

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