4.7 Article

Mechanism and Origins of Enantioselectivity of Cobalt-Catalyzed Intermolecular Hydroarylation/Cyclization of 1,6-Enynes with N-Pyridylindoles

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 87, Issue 9, Pages 6438-6443

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.2c00305

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Funding

  1. National Natural Science Foundation of China [22073066, 21503143, 21975179]

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Density functional theory calculations were used to investigate the cobalt-catalyzed intermolecular hydro-arylation/cyclization reaction. The computations revealed that the reaction proceeds through an oxidative cyclization of 1,6-enynes, followed by metal-assisted sigma-bond metathesis/reductive elimination, leading to the final hydroarylation/cyclization product. The steric repulsion and pi···pi interaction were found to be crucial in determining the observed enantioselectivity.
Density functional theory calculations were per-formed to investigate the cobalt-catalyzed intermolecular hydro-arylation/cyclization of 1,6-enynes withN-pyridylindoles. Thecomputations reveal that the reaction begins with the oxidativecyclization of 1,6-enyne to afford thefive-membered cobaltacycle,from which the metal-assisted Sigma-bond metathesis/C-C reductiveelimination led to thefinal hydroarylation/cyclization product. Theinitial oxidative cyclization constitutes the rate-determining step of the overall reaction. The steric repulsion and pi middotmiddotmiddot pi interactionwere found to play a crucial role in dictating the experimentally observed enantioselectivity

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