Unprecedented C-F/C-H Double-Insertion by Ni(0)

Nickel-catalyzed C-F activations enabled chemo-divergent C-C formation with alkynes by chelation assistance. The judicious choice of the al-kynes electronic properties allowed the selective synthesis of double-insertion aromatic homologation or alkyne mono-annulation products by C-F/C-H activation. Based on the unambiguous crystallographic characterization of an unprecedented 9-membered nickelocyclic intermediate and extensive DFT studies, a plausible mechanistic rationale was established for the selective C-F activation and the chemo-divergent catalysis. The paper was published recently in ACS Catalysis:

L. Capdevila, T. H. Meyer, S. Roldán-Gómez, J. M. Luis, L. Ackermann and X. Ribas
“Chemo-Divergent Nickel(0)-Catalyzed Arene C–F Activation with Alkynes: Unprecedented C-F/C-H Double-Insertion”
ACS Catal. 2019, ASAP [abstract]
DOI: 10.1021/acscatal.9b03620