Continuous Flow Sodiation of Substituted Acrylonitriles, Alkenyl Sulfides and Acrylates
Johannes H. Harenberg, Niels Weidmann, Konstantin Karaghiosoff, Paul Knochel
Abstract
Abstract The sodiation of substituted acrylonitriles and alkenyl sulfides in a continuous flow set‐up using NaDA (sodium diisopropylamide) in EtNMe 2 or NaTMP (sodium 2,2,6,6‐tetramethylpiperidide)⋅TMEDA in n‐hexane provides sodiated acrylonitriles and alkenyl sulfides, which are subsequently trapped in batch with various electrophiles such as aldehydes, ketones, disulfides and allylic bromides affording functionalized acrylonitriles and alkenyl sulfides. This flow‐procedure was successfully extended to other acrylates by using Barbier‐type conditions.
Topics & Concepts
ChemistryElectrophileHexaneAllylic rearrangementLithium diisopropylamideMedicinal chemistrySodiumContinuous flowOrganic chemistryCatalysisIonMechanicsDeprotonationPhysicsInnovative Microfluidic and Catalytic Techniques InnovationChemical Synthesis and ReactionsOxidative Organic Chemistry Reactions