Chemodivergent Nickel(0)-Catalyzed Arene C–F Activation with Alkynes: Unprecedented C–F/C–H Double Insertion

Nickel-catalyzed C–F activations enabled chemodivergent C–C formation with alkynes by chelation assistance. The judicious choice of the alkyne electronic properties allowed the selective synthesis of double-insertion aromatic homologation or alkyne monoannulation products by C–F/C–H activation. On t...

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Bibliographic Details
Published in:ACS catalysis 2019-12, Vol.9 (12), p.11074-11081
Main Authors: Capdevila, Lorena, Meyer, Tjark H, Roldán-Gómez, Steven, Luis, Josep M, Ackermann, Lutz, Ribas, Xavi
Format: Article
Language:English
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Summary:Nickel-catalyzed C–F activations enabled chemodivergent C–C formation with alkynes by chelation assistance. The judicious choice of the alkyne electronic properties allowed the selective synthesis of double-insertion aromatic homologation or alkyne monoannulation products by C–F/C–H activation. On the basis of the unambiguous crystallographic characterization of an unprecedented nine-membered nickelacyclic intermediate and extensive DFT studies, a plausible mechanistic rationale was established for the selective C–F activation and the chemodivergent catalysis.
ISSN:2155-5435
2155-5435
DOI:10.1021/acscatal.9b03620