A systematic study addressed toward the optimization of the Pd-catalyzed alkylation of indoles by allylic carbonates is presented. The protocol uses a catalytic amt. of [PdCl(p-allyl)]2/phosphine as a promoting agent, providing allylindoles, e.g. I (R = Ph, Me), in excellent yields. The regioselectivity of the reaction can be controlled by a proper choice of the base and the reaction media. The method proved to be effective also for intramol. allylic alkylations of indolyl carbonates, providing a flexible route to fused indole alkaloids.
M. BANDINI, A. MELLONI, UMANI RONCHI A. (2004). New Versatile Pd-Catalyzed Alkylation of Indoles via Nucleophilic Allylic Substitution. In controlling the Regioselectivity. ORGANIC LETTERS, 6, 3199-3202 [10.1021/ol048663z].
New Versatile Pd-Catalyzed Alkylation of Indoles via Nucleophilic Allylic Substitution. In controlling the Regioselectivity
BANDINI, MARCO;MELLONI, ALFONSO;UMANI RONCHI, ACHILLE
2004
Abstract
A systematic study addressed toward the optimization of the Pd-catalyzed alkylation of indoles by allylic carbonates is presented. The protocol uses a catalytic amt. of [PdCl(p-allyl)]2/phosphine as a promoting agent, providing allylindoles, e.g. I (R = Ph, Me), in excellent yields. The regioselectivity of the reaction can be controlled by a proper choice of the base and the reaction media. The method proved to be effective also for intramol. allylic alkylations of indolyl carbonates, providing a flexible route to fused indole alkaloids.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
