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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

Authors

    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
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Further Information

Publication History

Publication Date:
18 October 2019 (online)

 
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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.


 

 


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