Divergence between organometallic and single-electron-transfer mechanisms in copper (II)-mediated aerobic C–H oxidation

AM Suess, MZ Ertem, CJ Cramer…

Index: Suess, Alison M.; Ertem, Mehmed Z.; Cramer, Christopher J.; Stahl, Shannon S. Journal of the American Chemical Society, 2013 , vol. 135, # 26 p. 9797 - 9804

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Citation Number: 157

Abstract

Copper (II)-mediated C–H oxidation is the subject of extensive interest in synthetic chemistry, but the mechanisms of many of these reactions are poorly understood. Here, we observe different products from CuII-mediated oxidation of N-(8-quinolinyl) benzamide, depending on the reaction conditions. Under basic conditions, the benzamide group undergoes directed C–H methoxylation or chlorination. Under acidic conditions, the ...