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Synthesis of Tricyclic Heterocycles via a Tandem Aryl Alkylation/Heck Coupling Sequence

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journal contribution
posted on 02.02.2007, 00:00 by Dino Alberico, Alena Rudolph, Mark Lautens
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.

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