PDF icon Download PDF
Synfacts 2019; 15(11): 1259
DOI: 10.1055/s-0039-1690320
Metals in Synthesis
© Georg Thieme Verlag Stuttgart · New York

Asymmetric C–H Alkylation of Fluoroarenes with Alkenes via Nickel/NHC Catalysis

Contributor(s):
Mark Lautens
,
Randy Sanichar
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
CrossrefPubMedSearch in Google Scholar
Further Information

Publication History

Publication Date:
18 October 2019 (online)

 
 PDF Download Permissions and Reprints

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.


 

 


  Permissions and Reprints