Through-Space 1,4-Palladium Migration and 1,2-Aryl Shift: Direct Access to Dibenzo[a,c]carbazoles through a Triple CH Functionalization Cascade

Autor:	Samir Kumar Bhunia, Ranjan Jana, Ramalingam Natarajan, Arghya Polley
Rok vydání:	2015
Předmět:	Indole test Annulation Stereochemistry Aryl Organic Chemistry chemistry.chemical_element General Chemistry Catalysis chemistry.chemical_compound chemistry Intramolecular force Electrophile Moiety Bond cleavage Palladium
Zdroj:	Chemistry - A European Journal. 21:16786-16791
ISSN:	0947-6539
DOI:	10.1002/chem.201503474
Popis:	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.
Databáze:	OpenAIRE
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