Ligand-free copper-catalyzed regio- and stereoselective 1,1-alkylmonofluoroalkylation of terminal alkynes?

Chemical Communications Pub Date: 2020-09-22 DOI: 10.1039/D0CC05887D

Abstract

The copper-catalyzed highly regio- and stereoselective 1,1-alkylmonofluoroalkylation of terminal alkynes with α-chloroacetamides and dialkyl 2-fluoromalonate or 2-fluoro-N,N-dialkyl-3-oxobutanamide without an external ligand has been realized. With this novel methodology, (E)-β-monofluoroalkyl-β,γ-unsaturated amides containing quaternary C–F centers can be easily constructed in good to excellent yields.

Graphical abstract: Ligand-free copper-catalyzed regio- and stereoselective 1,1-alkylmonofluoroalkylation of terminal alkynes
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