Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 21, Issue 47, Pages 16786-16791Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201503474
Keywords
annulation; cascade reactions; C-H activation; carbazoles; palladium
Categories
Funding
- DST [SR/S2/RJN-97/2012]
- CSIR (miND) [BSC 0115]
- DST of the Government of India [SR/S2/RJN-62/2012]
- UGC
- CSIR
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A palladium-catalyzed expeditious synthesis of dibenzofused carbazoles from readily available 2-arylindoles and diaryliodonium salts is reported. Interestingly, after the electrophilic C3 palladation of indole, an unexpected through-space 1,4-palladium migration to the 2-aryl moiety, by remote C-H bond activation followed by C-H arylation with diaryliodonium salt, and an unprecedented 1,2-aryl shift take place. Finally, an intramolecular cross-dehydrogenative coupling (CDC) at the C2 position affords dibenzo[a,c]carbazoles in high yields. Remarkably, the present migratory annulation occurs through three C-H bond activation one C-C bond cleavage, and the simultaneous construction of three new C-C bonds in a single operation.
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