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Palladium-Catalyzed Intramolecular ipso-Friedel–Crafts Alkylation of Phenols and Indoles: Rearomatization-Assisted Oxidative Addition


  • This work was supported by Grant-in Aid for Scientific Resarch from the JSPS (Japan), the Research Foundation for Pharmaceutical Sciences, Chiba Univsersity, and the Inohana Foundation (Chiba University).


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Inspiroation: A novel synthesis of spirocycles based on a palladium-catalyzed intramolecular ipso-Friedel–Crafts alkylation of phenols (see scheme; dba=dibenzylideneacetone) and indoles is described. Mechanistic studies show that the reaction proceeds through an unprecedented rearomatization-assisted oxidative addition.

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