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Palladium-Catalyzed Hydride Addition/C-H Bond Activation Cascade: Cycloisomerization of 1,6-Diynes.

José F RodríguezKatherine I BurtonIvan FranzoniDavid A PetroneIna ScheipersMark Lautens
Published in: Organic letters (2018)
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.
Keyphrases
  • ionic liquid
  • energy transfer
  • genetic diversity