Palladium‐Assisted “Aromatic Metamorphosis” of Dibenzothiophenes into Triphenylenes |
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| Authors: | Dr. Dhananjayan Vasu Prof. Dr. Hideki Yorimitsu Prof. Dr. Atsuhiro Osuka |
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| Affiliation: | 1. Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo‐ku, Kyoto 606‐8502 (Japan);2. ACT‐C, JST, Sakyo‐ku, Kyoto 606‐8502 (Japan) |
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| Abstract: | 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 SN2 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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| Keywords: | C H arylation C S cleavage cross‐coupling palladium sulfur |
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