Palladium-Catalyzed Alkylation-Alkenylation Reactions: Rapid Access to Tricyclic Mescaline Analogues
Synlett October 25, 2006 DOI: 10.1055/s-2006-941583 via OpenAlex
Summary
AI-generated from the abstractA one-pot catalytic sequence uses palladium and norbornene to form two alkyl-aryl bonds and one alkenyl-aryl bond simultaneously. Starting from a Heck acceptor and an aryl iodide with two attached alkyl bromides, the method produces a range of symmetrical and unsymmetrical tricyclic heterocycles in good yields. The approach was demonstrated by synthesizing a tricyclic analogue of mescaline.
Study at a glance
| Characteristics | Methodology paper Peer reviewed |
|---|---|
| Topics | Mescaline |
| Keywords | Aryl Tricyclic Palladium Norbornene Alkylation |
| Citations | 10 |
| Key finding | A norbornene-mediated palladium-catalyzed cascade forms two alkyl-aryl and one alkenyl-aryl bond in one pot, enabling synthesis of tricyclic heterocycles and a mescaline analogue. |
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.