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Article Dans Une Revue Journal of the American Chemical Society Année : 2022

Cobalt-Catalyzed Enantioselective C-H Arylation of Indoles

Résumé

Atropoisomeric (hetero)biaryls are scaffolds with increasing importance in the pharmaceutical and agrochemical industries. Although it is the most obvious disconnection to construct such compounds, the direct enantioselective C-H arylation through the concomitant induction of the chiral information remains extremely challenging and uncommon. Herein, the unprecedented earth-abundant 3d-metal-catalyzed atroposelective direct arylation is reported, furnishing rare atropoisomeric C2-arylated indoles. Kinetic studies and DFT computation revealed an uncommon mechanism for this asymmetric transformation, with the oxidative addition being the rate-and enantio-determining step. Excellent stereoselectivities were reached (up to 96% ee), while using an unusual N-heterocyclic carbene-ligand bearing essential remote substituent. Attractive dispersion interactions along with positive C-H-π interactions exerted by the ligand were identified as key factors to guarantee the excellent enantioselection.
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Dates et versions

hal-03874366 , version 1 (28-11-2022)

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Nicolas Jacob, Yassir Zaid, João C A Oliveira, Lutz Ackermann, Joanna Wencel-Delord. Cobalt-Catalyzed Enantioselective C-H Arylation of Indoles. Journal of the American Chemical Society, 2022, ⟨10.1021/jacs.1c09889⟩. ⟨hal-03874366⟩
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