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Distortion/Interaction analysis reveals the origins of selectivities in iridium-catalyzed C-H borylation of substituted arenes and 5-membered heterocycles.

  • Author(s): Green, Aaron G
  • Liu, Peng
  • Merlic, Craig A
  • Houk, KN
  • et al.

Published Web Location

https://doi.org/10.1021/ja411699u
Abstract

The iridium-catalyzed borylation of mono- and disubstituted arenes and heteroarenes has been studied with density functional theory. The distortion/interaction model was employed to understand the origins of selectivities in these reactions. Computations revealed that the transition states for C-H oxidative addition are very late, resembling the aryl iridium hydride intermediate with a fully formed Ir-C bond. Consequently, the regioselectivity is mainly controlled by differences in the interaction energies between the iridium catalyst and arene carbon.

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