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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

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.


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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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