Copper-catalyzed radical trans-selective hydroboration of ynamides with N-heterocyclic carbene boranes

Vinylboron compounds are important compounds in organic chemistry and biology. In this communication, we developed a copper(I)-catalyzed, highly regio- and stereoselective radical trans-hydroboration of ynamides with N-heterocyclic carbene (NHC)-ligated borane is reported, which leads to a series of trans-boryl enmides that can be conveniently transformed into various multi-substituted enamides. Further investigation showcased that our method is robust and scalable. The mechanism of this unique reaction is studied and discussed. [Display omitted] •A Cu-catalyzed highly regio- and stereoselective radical trans-hydroboration of ynamides•Good to excellent yields, good functional group tolerance•Further investigation showcased that our method is robust and scalable Catalysis; Organic chemistry; Organic synthesis