Proton-abstraction mechanism in the palladium-catalyzed intramolecular arylation: Substituent effects

Domingo García-Cuadrado, Paula De Mendoza, Ataualpa A.C. Braga, Feliu Maseras, Antonio M. Echavarren

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The regioselectivity observed in the intramolecular palladium-catalyzed arylation of substituted bromobenzyldiarylmethanes as well as theoretical results demonstrate that the Pd-catalyzed arylation proceeds by a mechanism involving a proton abstraction by the carbonate, or a related basic ligand. The reaction is facilitated by electron-withdrawing substituents on the aromatic ring, which is inconsistent with an electrophilic aromatic-substitution mechanism. The more important directing effect is exerted by electron-withdrawing substituents ortho to the reacting site. © 2007 American Chemical Society.
Original languageEnglish
Pages (from-to)6880-6886
JournalJournal of the American Chemical Society
Issue number21
Publication statusPublished - 30 May 2007

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