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.

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.
2004
M. BANDINI; A. MELLONI; UMANI RONCHI A.
File in questo prodotto:
Eventuali allegati, non sono esposti

I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.

Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11585/1857
 Attenzione

Attenzione! I dati visualizzati non sono stati sottoposti a validazione da parte dell'ateneo

Citazioni
  • ???jsp.display-item.citation.pmc??? 14
  • Scopus 154
  • ???jsp.display-item.citation.isi??? 150
social impact