The versatile role of norbornene in C-H functionalization processes: concise synthesis of tetracyclic fused pyrroles via a threefold domino reaction |
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| Authors: | Kersten M Gericke |
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| Institution: | Department of Chemistry, Davenport Chemical Laboratories, University of Toronto, 80 St. George Street, Toronto, ON M5S 3H6, Canada |
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| Abstract: | The synthesis of novel tetracyclic fused pyrroles from 1-(2-iodophenyl)-1H-pyrrole and various bromoalkyl-aryl alkynes via a palladium(0)-catalyzed and norbornene-mediated threefold domino reaction is reported. PdCl2 and tri-2-furylphosphine (TFP) in the presence of norbornene and Cs2CO3 in CH3CN at 90 °C gave a variety of tetracyclic fused pyrroles in usually high yields. In the described reaction sequence two of the three carbon-carbon bonds are formed by functionalization of an unactivated aryl C-H bond. |
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| Keywords: | C-H activation Domino reaction Palladium Catalysis Norbornene ortho-Functionalization Fused pyrroles Catellani reaction |
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