1428962-05-3Relevant academic research and scientific papers
Palladium-catalyzed intramolecular ipso-Friedel-Crafts alkylation of phenols and indoles: Rearomatization-assisted oxidative addition
Nemoto, Tetsuhiro,Zhao, Zengduo,Yokosaka, Takuya,Suzuki, Yuta,Wu, Riliga,Hamada, Yasumasa
supporting information, p. 2217 - 2220 (2013/03/28)
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. Copyright
Synthesis of spiro[4.5]cyclohexadienones with an allene motif via a base-promoted intramolecular ipso-Friedel-Crafts addition of phenols to propargyl bromides
Nemoto, Tetsuhiro,Wu, Riliga,Zhao, Zengduo,Yokosaka, Takuya,Hamada, Yasumasa
, p. 3403 - 3409 (2013/04/24)
We developed a novel synthetic method for allenyl spiro[4.5] cyclohexadienone derivatives based on a base-promoted intramolecular ipso-Friedel-Crafts addition of phenols to propargyl bromides. The present spirocyclization proceeded in a CH2Cl2-tert-BuOH mixed solvent system using potassium tert-butoxide as the base, and produced the corresponding spiro[4.5]cyclohexadienone derivatives with an allene motif in up to 99% yield. This-type allenyl spirocycle was also accessible through Pd-catalyzed intramolecular ipso-Friedel-Crafts alkylation when a propargyl carbonate derivative with a naphthol unit was used as a substrate. Acid-promoted skeletal rearrangement of the reaction adducts was also examined.
