Synthesis of Tricyclic Heterocycles via a Tandem Aryl Alkylation/Heck Coupling Sequence
The Journal of Organic Chemistry – December 29, 2006
Source: OpenAlex
Summary
A groundbreaking method enables the synthesis of complex tricyclic heterocycles in a single step, achieving two alkyl-aryl bonds and one alkenyl-aryl bond using microwave irradiation. This innovative palladium-catalyzed sequence involves 20 different aryl iodides and generates symmetrical and unsymmetrical compounds containing oxygen, nitrogen, silicon, and sulfur. Notably, this technique was successfully applied to create a tricyclic mescaline analogue, showcasing its potential in combinatorial chemistry and organic synthesis for producing diverse chemical structures efficiently.
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 with use of microwave irradiation. A variety of symmetrical and unsymmetrical oxygen-, nitrogen-, silicon-, and sulfur-containing tricyclic heterocycles were synthesized from a Heck acceptor and an aryl iodide containing two tethered alkyl halides. This approach was further applied to the synthesis of a tricyclic mescaline analogue.