Catalyst and base controlled site-selective sp 2 and sp 3 direct arylation of azine N-oxides

DJ Schipper, LC Campeau, K Fagnou

Index: Schipper, Derek J.; Campeau, Louis-Charles; Fagnou, Keith Tetrahedron, 2009 , vol. 65, # 16 p. 3155 - 3164

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Citation Number: 86

Abstract

Site-selective direct arylation of both sp2 and sp3 sites on azine N-oxide substrates is described. The arylation reactions are carried out in either a divergent manner or a sequential manner. The sp3 arylation reaction is applied to the synthesis of the natural products, papaverine and crykonisine, and a rationale for low reactivity of electron-deficient aryl halides is provided. Mechanistic investigations point toward the intimate involvement ...