Proton-Abstraction Mechanism in the Palladium-Catalyzed Intramolecular Arylation: Substituent Effects
Journal of the American Chemical Society2007Vol. 129(21), pp. 6880–6886
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Domingo García‐Cuadrado, Paula de Mendoza, Ataualpa Albert Carmo Braga, Feliu Maseras, Antonio M. Echavarren
Abstract
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.
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