Stereoselective Synthesis of (Z)-Acrylic Nitriles from the Ruthenium-Catalyzed Coupling Reaction of Nitriles with Unsaturated Carbonyl Compounds via C–C Bond Cleavage

Acrylic nitriles are a versatile class of synthetic precursors for a variety of pharmaceutically active compounds, as well as for nitrile polymers. We devised a stereoselective synthesis of (Z)-acrylic nitriles from the Ru-catalyzed coupling reaction of nitriles with unsaturated carbonyl compounds via C-C bond cleavage. Both carbon KIE and Hammett correlation data indicated that C-C bond cleavage is the rate-determining step for the coupling reaction. Several bioactive (Z)-acrylic nitriles were synthesized by using the catalytic coupling method.