Journal Article Palladium-assisted "aromatic metamorphosis" of dibenzothiophenes into triphenylenes.

Vasu, Dhananjayan  ,  Yorimitsu, Hideki  ,  Osuka, Atsuhiro

54 ( 24 )  , pp.7162 - 7166 , 2015-05-04 , wiley
Two new palladium-catalyzed reactions of aromatic sulfur compounds enabled the conversion of dibenzothiophenes into triphenylenes in four steps. This transformation of one aromatic framework into another consists of 1) 4-chlorobutylation of the dibenzothiophene to form the corresponding sulfonium salt, 2) palladium-catalyzed arylative ring opening of the sulfonium salt with a sodium tetraarylborate, 3) an intramolecular S(N)2 reaction to form a teraryl sulfonium salt, and 4) palladium-catalyzed intramolecular C-S/C-H coupling through electrophilic palladation. Symmetrical as well as unsymmetrical triphenylenes of interest were synthesized in a tailor-made fashion in satisfactory overall yields.

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