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Journal of the American Chemical Society

Journal of the American Chemical Society

IF: 14.4
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Palladium-Catalyzed Benzene Arylation:? Incorporation of Catalytic Pivalic Acid as a Proton Shuttle and a Key Element in Catalyst Design

Published:9 December 2006 DOI: 10.1021/ja067144j PMID: 17177387
Marc Lafrance, Keith Fagnou

Abstract

A palladium?pivalic acid cocatalyst system has been developed that exhibits unprecedented reactivity in direct arylation. This reactivity is illustrated with the first examples of high yielding direct metalation?arylation reactions of a completely unactivated arene, benzene. Experimental and computational evidence indicates that the pivalate anion is a key component in the palladation/C?H bond breaking event, that it lowers the energy of C?H bond cleavage and acts as a catalytic proton shuttle from benzene to the stoichiometric carbonate base. Eight examples of substituted aryl bromides are included which undergo direct arylation with benzene in 55?85% yield.

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Benzene 71-43-2 C6H6 745 suppliers $11.20-$4420.00
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Pivalic acid 75-98-9 C5H10O2 508 suppliers $7.62-$4482.37
silver pivalate 7324-58-5 C5H9AgO2 14 suppliers Inquiry

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