Distortion/interaction analysis reveals the origins of selectivities in iridium-catalyzed C-H borylation of substituted arenes and 5-membered heterocycles
- Author(s): Green, AG
- Liu, P
- Merlic, CA
- Houk, KN
- et al.
Published Web Locationhttps://doi.org/10.1021/ja411699u
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. © 2014 American Chemical Society.
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