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Selective ortho-C−H Activation in Arenes without Functional Groups

Research output: Contribution to Journal/MagazineJournal articlepeer-review

  • Antony Chan
  • Martin Jakoobi
  • Chenxu Wang
  • Robert O'Neill
  • Gulsevim Aydin
  • Nathan Halcovitch
  • Roman Boulatov
  • Alexey Sergeev
<mark>Journal publication date</mark>6/07/2022
<mark>Journal</mark>Journal of the American Chemical Society
Issue number26
Number of pages5
Pages (from-to)11564–11568
Publication StatusPublished
Early online date21/06/22
<mark>Original language</mark>English


Aromatic C-H activation in alkylarenes is a key step for the synthesis of functionalised organic molecules from simple hydrocarbon precursors. Known examples of such C-H activations often yield mixtures of products resulting from activation of least-hindered C-H bonds. Here we report highly selective ortho-C-H activation in alkylarenes by simple iridium complexes. We demon-strate that the capacity of the alkyl substituent to override the typical preference of metal-mediated C-H activation for least hindered aromatic C-H bonds results from transient insertion of iridium into the benzylic C-H bond. This enables fast iridium insertion into the ortho-C-H bond, followed by regeneration of the benzylic C-H bond by reductive elimination. Bulkier alkyl substituents increase ortho-selectivity. The described chemistry comprises a conceptually new alternative to existing approaches to aromatic C-H bond activation.