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  • Title: New versatile Pd-catalyzed alkylation of indoles via nucleophilic allylic substitution: controlling the regioselectivity.
    Author: Bandini M, Melloni A, Umani-Ronchi A.
    Journal: Org Lett; 2004 Sep 02; 6(18):3199-202. PubMed ID: 15330622.
    Abstract:
    [reaction: see text] A systematic study addressed toward the optimization of the Pd-catalyzed alkylation of indoles by allylic carbonates is presented. The protocol uses a catalytic amount of [PdCl(pi-allyl)](2)/phosphine as a promoting agent, providing allylindoles 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 intramolecular allylic alkylations of indolyl carbonates, providing a flexible route to fused indole alkaloids.
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