Regio- and Stereoselective Reductive Coupling of Alkynes and Crotononitrile
Kun Cui, Yanlin Li, Gongqiang Li, Ji‐Bao Xia
Abstract
A new regio- and stereoselective reductive coupling of alkynes and crotononitrile has been developed via visible light organophotoredox cobalt dual catalysis. A variety of enantioenriched homoallylic nitriles bearing a stereodefined trisubstituted alkene have been easily synthesized with good to excellent regio- (up to >20:1 rr), stereo- (>20:1 E / Z ), and enantioselectivity (up to 98% ee) control under mild conditions. The corresponding nitrile products were smoothly converted into various chiral building blocks. Remarkably, a simple organic base together with water have been utilized as hydrogen sources in this photoinduced reductive reaction.
Topics & Concepts
ChemistryStereoselectivityNitrileAlkeneCatalysisCombinatorial chemistryRegioselectivityCobaltReductive eliminationOrganic chemistryCatalytic C–H Functionalization MethodsRadical Photochemical ReactionsOxidative Organic Chemistry Reactions