Directed Metal (Oxo) Aliphatic C–H Hydroxylations: Overriding Substrate Bias

MA Bigi, SA Reed, MC White

Index: Paradine, Shauna M.; White, M. Christina Journal of the American Chemical Society, 2012 , vol. 134, # 4 p. 2036 - 2039

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Citation Number: 78

Abstract

The first general strategy for a directing effect on metal (oxo)-promoted C–H hydroxylations is described. Carboxylic acid moieties on the substrate overcome unfavorable electronic, steric, and stereoelectronic biases in C–H hydroxylations catalyzed by the non-heme iron complex Fe (PDP). In a demonstration of the power of this directing effect, C–H oxidation is diverted away from an electronically favored C-1 H abstraction/rearrangement pathway in ...