Copper-catalyzed C-N coupling of amides and nitrogen-containing heterocycles in the presence of cesium fluoride

The copper-catalyzed C-N coupling of amides to aryl halides usually requires the use of strong alkali metal bases, such as K2CO3, K3PO4, and Cs2CO3, at high temperature. We discovered that CsF is sufficiently basic to promote the cross-coupling of amides and carbamates with aryl halides. Most aryl iodides coupled in high yield at room temperature. This alternative base may be a suitable replacement for substrates that are incompatible with high temperature and strongly basic conditions and can further enhance the chemoselectivity of this reaction.

Cesium fluoride as the base efficiently enables the copper-catalyzed N-arylation of amides and nitrogen heterocycles.