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Pd-Catalyzed Cascade Intramolecular Heck Cyclization/Dearomatization of Indoles for the Construction of Two All-Carbon Quaternary Centers.

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A facile Pd-catalyzed cascade of intramolecular Heck cyclization/alkylpalladium activated dearomatization of aryl alkyne-tethered indole is described. In this single step two nonadjacent all-carbon quaternary centers, two nitrogen-containing heterocycles, and three… Click to show full abstract

A facile Pd-catalyzed cascade of intramolecular Heck cyclization/alkylpalladium activated dearomatization of aryl alkyne-tethered indole is described. In this single step two nonadjacent all-carbon quaternary centers, two nitrogen-containing heterocycles, and three C(sp2)-C(sp3) bonds are efficiently furnished. These products could also undergo 5-to-6 ring migration-expansion reaction under Brønsted-acid conditions to transform into the benzo[c]carbazole skeletons.

Keywords: intramolecular heck; catalyzed cascade; cascade intramolecular; carbon quaternary; heck cyclization; quaternary centers

Journal Title: Organic letters
Year Published: 2022

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