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.
A regioselective synthesis of symmetrical and unsymmetrical benzopinacolones through aerobic dehydrogenative α-arylation at the tertiary sp(3) 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 sp(3) C-H bond of 1,1-diphenylketone. Subsequent α-arylation was achieved at the methene sp(3) 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.
Department of Chemistry, Indian Institution of Science Education and Research, Pune 411021, Maharashtra (India), Fax: (+91) 20-25865315.
Nagnath Yadav
NY
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Masilamani
M
Jeganmohan
D000475:Alkenes / Q000737:chemistry*; D002074:Butanones / Q000138:chemical synthesis / Q000737:chemistry*; D002244:Carbon / Q000737:chemistry; D006859:Hydrogen / Q000737:chemistry; D007659:Ketones / Q000737:chemistry*; D011084:Polycyclic Aromatic Hydrocarbons / Q000737:chemistry*; D011789:Quantum Theory; D013237:Stereoisomerism
D000475:Alkenes; D002074:Butanones; D007659:Ketones; D011084:Polycyclic Aromatic Hydrocarbons; C084935:pinacolone; D002244:Carbon; D006859:Hydrogen
CH activation; aromatic substitution; arylation; carbocations; radical reactions