Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 18, Issue 17, Pages 5352-5360Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201103819
Keywords
C?H bond activation; domino reactions; heterocycles; palladium; polycycles
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Funding
- Ministry of Education, Culture, Sports, Science and Technology of Japan
- Grants-in-Aid for Scientific Research [22106521, 23790130, 22590005, 24590008, 22390021] Funding Source: KAKEN
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Palladium-catalyzed cascade C?H alkenylation and arylation provides convenient access to polycyclic aromatic compounds. Treatment of 3-bromoaniline derivatives bearing a bromocinnamyl group on the nitrogen atom with a catalytic amount of [Pd(OAc)2] and PCy3 center dot HBF4 in the presence of Cs2CO3 in dioxane affords naphthalene-fused indole derivatives in good yields. This double cyclization reaction is also applicable to heterocyclic substrates, giving fused indoles containing a heteroaromatic ring such as dibenzofuran, dibenzothiophene, carbazole, indole, or benzofuran through heterocyclic C-H arylation. When using a 2,6-unsubstituted aniline derivative, the first C-H arylation preferentially proceeds at the more hindered position of the aniline ring.
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