Palladium-Catalyzed Alkylation-Alkenylation Reactions: Rapid Access to Tricyclic Mescaline Analogues
Synlett – October 25, 2006
Source: OpenAlex
Summary
A new palladium-catalyzed method efficiently creates two alkyl-aryl bonds and one alkenyl-aryl bond in a single step, achieving yields of up to 90% with 15 different symmetrical and unsymmetrical tricyclic heterocycles. This innovative approach utilizes norbornene and integrates a Heck acceptor with an aryl iodide featuring tethered alkyl bromides. Notably, it successfully synthesizes a tricyclic mescaline analogue, showcasing its potential in organic and medicinal chemistry for developing complex compounds through catalytic cross-coupling reactions and C–H functionalization methods.
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.