A general modular method of azaindole and thienopyrrole synthesis via Pd-catalyzed tandem couplings of gem-dichloroolefins.
A palladium-catalyzed reaction of gem-dichloroolefins and a boronic acid via a tandem intramolecular C-N and intermolecular Suzuki coupling process gave corresponding substituted azaindoles or thienopyrroles. This method is a very modular protocol to synthesize all four isomers of azaindole and two isomers of thienopyrroles in good to excellent yield.
Fang
Yuan-Qing
YQ
Davenport Chemistry Laboratories, Department of Chemistry, University of Toronto, 80 St. George Street, Toronto, Ontario, M5S 3H6, Canada.
Yuen
Josephine
J
Lautens
Mark
M
D000475:Alkenes / Q000737:chemistry*; D001372:Aza Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D002713:Chlorine / Q000737:chemistry*; D007211:Indoles / Q000737:chemistry*; D008958:Models, Molecular; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry*; D011758:Pyrroles / Q000138:chemical synthesis* / Q000737:chemistry
D000475:Alkenes; D001372:Aza Compounds; D007211:Indoles; D011758:Pyrroles; C521801:thienopyrrole; D002713:Chlorine; D010165:Palladium