Sequential Oxidative Transformation of Tetraarylethylenes to 9,10-Diarylphenanthrenes and Dibenzo[g,p]chrysenes using DDQ as an Oxidant

Tetraarylethylenes can be sequentially transformed into 9,10-diarylphenanthrenes and dibenzo[g,p]chrysenes using 1 and 2 equiv of DDQ, respectively, in CH2Cl2 containing methanesulfonic acid, in excellent yields. Efficient access to substituted dibenzochrysenes from tetraarylethylenes establishes th...

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Bibliographic Details
Published in:Organic letters 2011-04, Vol.13 (7), p.1634-1637
Main Authors: Navale, Tushar S, Thakur, Khushabu, Rathore, Rajendra
Format: Article
Language:English
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Summary:Tetraarylethylenes can be sequentially transformed into 9,10-diarylphenanthrenes and dibenzo[g,p]chrysenes using 1 and 2 equiv of DDQ, respectively, in CH2Cl2 containing methanesulfonic acid, in excellent yields. Efficient access to substituted dibenzochrysenes from tetraarylethylenes establishes the versatility of this procedure over the existing multistep syntheses of dibenzochrysenes. Moreover, the ready regeneration of DDQ from easily recovered reduced DDQ−H2 continues to advance the use of DDQ/H+ for the oxidative C−C bond forming reactions.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol200069c