Synlett 2006(18): 2969-2972  
DOI: 10.1055/s-2006-941583
LETTER
© Georg Thieme Verlag Stuttgart · New York

Palladium-Catalyzed Alkylation-Alkenylation Reactions: Rapid Access to Tricyclic Mescaline Analogues

Dino Alberico, Mark Lautens*
Davenport Research Laboratories, Department of Chemistry, University of Toronto, Toronto, Ontario, M5S 3H6, Canada
Fax: +1(416)9468185; e-Mail: mlautens@chem.utoronto.ca;
Further Information

Publication History

Received 16 February 2006
Publication Date:
29 June 2006 (online)

Abstract

A norbornene-mediated palladium-catalyzed sequence is described in which two alkyl-aryl bonds and one alkenyl-aryl bond are formed in one pot. A variety of symmetrical and unsymmetrical tricyclic heterocycles were synthesized in good yields from a Heck acceptor and an aryl iodide containing two tethered alkyl bromides. This methodology was applied to the synthesis of a tricyclic mescaline analogue.