Base-Promoted Addition of Arylacetonitriles to Terminal Alkynes: Regio- and Stereoselective Access to Disubstituted Acrylonitriles

A base-promoted nucleophilic addition of arylacetonitriles to terminal alkynes has been described for the first time, providing a simple and straightforward protocol for the synthesis of a range of structurally diverse (Z)-2,3-disubstituted acrylonitriles in moderate to excellent yields. Of particular note, the transition metal-free carbon-carbon double bond forming reaction is regio- and stereoselective under mild conditions. A variety of functional groups can be tolerated on both the arylacetonitrile substrate and the alkyne coupling partner. Moreover, the reaction is easily scalable and the products thus obtained can serve as versatile intermediates for the synthesis of a series of useful substances.