Hydrofunctionalization of Propadiene – New Life for a Previously Unwanted Product
Simon V. Sieger, Ilja Lubins, Bernhard Breit
Abstract
A highly versatile palladium-catalyzed allylation reaction of several pronucleophiles is reported. The use of propadiene in toluene provides an atom economic and waste-free access to allylated nucleophiles, a structural motif with almost unlimited possibilities for further functionalization. In addition to N-, O-, and S-pronucleophiles, the Pd/BINAP system is capable of adding a C-pronuceophile to allene. A plausible mechanism is supported by deuterium labeling experiments.
Topics & Concepts
AlleneBINAPChemistryCatalysisNucleophilePalladiumCombinatorial chemistryDeuteriumToluenePhotochemistrySurface modificationOrganic chemistryEnantioselective synthesisPhysicsPhysical chemistryQuantum mechanicsAsymmetric Synthesis and CatalysisCatalytic C–H Functionalization MethodsCyclopropane Reaction Mechanisms