Palladium-catalyzed heteroannulation of cyclic alkenes by functionally substituted aryl iodides |
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Authors: | Daniel E Emrich |
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Institution: | Department of Chemistry, Iowa State University, Ames, IA 50011, USA |
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Abstract: | Indolines and 2,3-dihydrobenzofurans are produced in good yields by the Pd(0)-catalyzed heteroannulation of cyclic and bicyclic alkenes by o-amino- and o-hydroxyaryl iodides. These processes are only successful with cyclic olefins in which the key alkylpalladium intermediate cannot undergo facile palladium β-hydride elimination. These reactions appear to involve: (1) oxidative addition of the aryl iodide to the palladium catalyst, (2) arylpalladation of the olefin, (3) possible coordination of the internal nucleophile to the palladium, (4) formation of a six-membered palladacycle, and (5) reductive elimination of the organopalladium intermediate to give the heteroannulation product and regenerate Pd(0). |
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Keywords: | Palladium catalysis Heteroannulation Indolines Dihydrobenzofurans Cyclic alkenes |
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