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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 CH 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 CH 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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