Pd-catalyzed cascade carbopalladation-annulation reaction of 3-(2-iodobenzyl)-indoles into fused 6/5/7/6- and 6/5/5/6- heterocyclic systems.
Polycyclic indole structures, possessing fused seven-membered rings were efficiently synthesized via the Pd-catalyzed intramolecular carbopalladation-annulation of 3-(2-iodobenzyl)-indoles and alkynes. A remarkable base effect on the chemoselectivity of this transformation has been found: switching from Et(3)N to CsOAc completely reverses the reaction path to intramolecular cyclization forming fused five-membered rings.
Chernyak
Natalia
N
Department of Chemistry, University of Illinois, 845 West Taylor Street, Chicago, IL 60607, USA.
Tilly
David
D
Li
Zhou
Z
Gevorgyan
Vladimir
V
D000480:Alkynes / Q000737:chemistry; D002384:Catalysis; D003500:Cyclization; D006571:Heterocyclic Compounds / Q000737:chemistry*; D007211:Indoles / Q000737:chemistry*; D010165:Palladium / Q000737:chemistry*; D012545:Schiff Bases / Q000737:chemistry
D000480:Alkynes; D006571:Heterocyclic Compounds; D007211:Indoles; D012545:Schiff Bases; D010165:Palladium