Cai Y,
Ye X,
Liu S,
Shi S.-L.
* Shanghai Institute of Organic Chemistry, P. R. of China
Nickel/NHC-Catalyzed Asymmetric C–H Alkylation of Fluoroarenes with Alkenes: Synthesis
of Enantioenriched Fluorotetralins.
Angew. Chem. Int. Ed. 2019;
58: 13433-13437
Key words
hydroarylation - C–H alkylation - chiral NHC ligands - fluoroarenes - nickel catalysis
Significance
The authors demonstrate an unprecedented catalytic enantioselective C–H alkylation
of polyfluoroarenes. The annulation displayed complete endo selectivity, with exclusive C–H over C–F activation, and excellent enantioselectivity.
Comment
In addition to conferring excellent enantioselectivity, the use of the rather bulky
chiral N-heterocyclic carbene ligand for the nickel catalyst prevented any competition
from C–F activation; as such, there was complete chemo- and regioselectivity.
