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

…, SI Gorelsky, DR Stuart, LC Campeau…

Index: Sun, Ho-Yan; Gorelsky, Serge I.; Stuart, David R.; Campeau, Louis-Charles; Fagnou, Keith Journal of Organic Chemistry, 2010 , vol. 75, # 23 p. 8180 - 8189

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Citation Number: 132

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 ...

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