Palladium-Catalyzed Hydride Addition/C-H Bond Activation Cascade: Cycloisomerization of 1,6-Diynes
José F Rodríguez1, Katherine I Burton1, Ivan Franzoni1
1Davenport Research Laboratories, Department of Chemistry , University of Toronto , 80 St. George Street , Toronto , Ontario M5S 3H6 , Canada.
Abstract:
The use of ammonium halide salts as metal hydride precursors in a new Pd-catalyzed cycloisomerization of 1,6-diynes, which affords unexplored silylated 2-azafluorenes, is reported. This cascade process includes the addition of a Pd-hydride species to a π-system, intramolecular carbopalladation, and C(sp2)-H bond activation. A variety of functional groups are tolerated, and the synthetic utility of the resulting products has been demonstrated by a series of derivatizations.
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