Synthesis of Tricyclic Heterocycles via a Tandem Aryl Alkylation/Heck Coupling Sequence
Dino Alberico, Alena Rudolph, Mark Lautens
The Journal of Organic Chemistry December 29, 2006 DOI: 10.1021/jo0617868 (opens in new tab)
Study at a glance
AI-extracted from the abstract| Characteristics | Methodological paper Peer reviewed |
|---|---|
| Keywords | Tandem Tricyclic Aryl Alkylation Sequence biology Heck reaction Coupling piping Combinatorial chemistry Stereochemistry Organic chemistry Catalysis Biochemistry Catalytic cross-coupling reactions |
| Citations | 60 |
| Key points | A norbornene-mediated palladium-catalyzed sequence enables one-pot formation of two alkyl-aryl and one alkenyl-aryl bonds to produce tricyclic heterocycles. |
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.