Synthesis of tricyclic heterocycles via a tandem aryl alkylation/heck coupling sequence.
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.
Alberico
Dino
D
Davenport Research Laboratories, Department of Chemistry, University of Toronto, 80 St. George Street, Toronto, Ontario, M5S 3H6, Canada.
Rudolph
Alena
A
Lautens
Mark
M
D000478:Alkylation; D002384:Catalysis; D003500:Cyclization; D006575:Heterocyclic Compounds, 3-Ring / Q000138:chemical synthesis*; D006846:Hydrocarbons, Halogenated / Q000737:chemistry; D007455:Iodine / Q000737:chemistry; D008956:Models, Chemical; D009584:Nitrogen / Q000737:chemistry; D009636:Norbornanes / Q000737:chemistry*; D017646:Organosilicon Compounds / Q000138:chemical synthesis; D010100:Oxygen / Q000737:chemistry; D010165:Palladium / Q000737:chemistry*; D013455:Sulfur / Q000737:chemistry
D006575:Heterocyclic Compounds, 3-Ring; D006846:Hydrocarbons, Halogenated; D009636:Norbornanes; D017646:Organosilicon Compounds; D010165:Palladium; D013455:Sulfur; D007455:Iodine; D009584:Nitrogen; D010100:Oxygen