Mechanistic analysis of azine N-oxide direct arylation: Evidence for a critical role of acetate in the Pd (OAc) 2 precatalyst

HY Sun, SI Gorelsky, DR Stuart…

Index: Gorelsky, Serge I.; Lapointe, David; Fagnou, Keith Journal of the American Chemical Society, 2008 , vol. 130, # 33 p. 10848 - 10849

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Citation Number: 131

Abstract

Detailed mechanistic studies on the palladium-catalyzed direct arylation of pyridine N- oxides are presented. The order of each reaction component is determined to provide a general mechanistic picture. The C− H bond cleaving step is examined in further detail through computational studies, and the calculated results are in support of an inner-sphere concerted metalation− deprotonation (CMD) pathway. Competition experiments were ...