Advanced Synthesis & Catalysis · 2012 · 56 citations · 55 references
Natural SciencesChemistryMedicinal ChemistryCatalysisOrganic ChemistrySynthetic Medicinal ChemistryHeterocycle SynthesisHeterocyclic ChemistryHeterocyclic CompoundsOrganic SynthesisAryl Halide CouplingFunctional Group ToleranceHeterocycle FunctionalizationStereoselective SynthesisStereoselectivity
Abstract A palladium‐catalyzed, one‐pot cyclization reaction to construct (3 E )‐(imino)isoindolin‐1‐ones and (3 E )‐(imino)thiaisoindoline 1,1‐dioxides by introducing ortho ‐reactive functional groups on aryl halides is reported. Under optimal conditions, the cyclization reaction afforded the corresponding products in good to excellent yields (up to 93%) with high stereoselectivity. Notably, this transformation successfully extends its application for the synthesis of phenanthridines and dibenzooxazepines. This new synthetic protocol not only extends the application platform for palladium‐catalyzed CC coupling of aryl halides with isocyanides, but also opens atom‐economic and step‐economic synthetic routes for nitrogen‐containing heterocyclic compounds with wide functional group compatibility.
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Seung Hwan Cho, J.‐Y. Yoon, Sukbok Chang · Journal of the American Chemical Society · 2011 · 513 citations