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J Am Chem Soc. 2007 May 30;129(21):6880-6. Epub 2007 Apr 27.

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

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1
Institute of Chemical Research of Catalonia, Av. Països Catalans 16, 43007 Tarragona, Spain.

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.

PMID:
17461585
DOI:
10.1021/ja071034a

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