Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 54, Issue 24, Pages 7162-7166Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201501992
Keywords
C-H arylation; C-S cleavage; cross-coupling; palladium; sulfur
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Funding
- MEXT [25107002]
- JSPS [24685007, 26620081]
- JSPS
- Grants-in-Aid for Scientific Research [25107002, 26620081, 24685007, 13F03036] Funding Source: KAKEN
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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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