50 research outputs found
Palladium-assisted "aromatic metamorphosis" of dibenzothiophenes into triphenylenes.
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)â
4-chlorobutylation of the dibenzothiophene to form the corresponding sulfonium salt, 2)â
palladium-catalyzed arylative ring opening of the sulfonium salt with a sodium tetraarylborate, 3)â
an intramolecular S(N)2 reaction to form a teraryl sulfonium salt, and 4)â
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