Iridium-catalyzed borylation of secondary C–H bonds in cyclic ethers

CW Liskey, JF Hartwig

Index: Liskey, Carl W.; Hartwig, John F. Journal of the American Chemical Society, 2012 , vol. 134, # 30 p. 12422 - 12425

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Citation Number: 65

Abstract

The borylation of secondary C–H bonds, specifically secondary C–H bonds of cyclic ethers, with a catalyst generated from tetramethylphenanthroline and an iridium precursor is reported. This borylation occurs with unique selectivity for the C–H bonds located β to the oxygen atoms over the weaker C–H bonds located α to oxygen atoms. Mechanistic studies imply that the C–H bond cleavage occurs directly at the β position rather than at the α ...