Aryl Silicon Nucleophiles in Bismuth Catalysis
Teresa Faber, Sophia Engelhardt, Josep Cornellà
Abstract
Abstract We present a catalytic protocol utilizing bismuth for the synthesis of aromatic fluorinated thiosulfones, showcasing a seminal example of aryl silicon nucleophiles in Bi catalysis. This catalytic process is enabled by a series of Bi‐based organometallic transformations, including an unprecedented transmetalation of aryl silicates to Bi(III) complexes and the formal migratory insertion of sulfur dioxide (SO 2 ) into the Bi‐C bond. The protocol is compatible with a wide range of anionic and neutral Ar‐Si compounds, including heterocycles. Stoichiometric investigations of individual organometallic steps provide strong evidence supporting a Bi‐redox‐neutral catalytic cycle.
Topics & Concepts
NucleophileCatalysisTransmetalationArylBismuthChemistryCatalytic cycleCombinatorial chemistryGroup 2 organometallic chemistryStoichiometryRedoxOrganic chemistryInorganic chemistryMoleculeAlkylSulfur-Based Synthesis TechniquesSynthesis and characterization of novel inorganic/organometallic compoundsChemical Synthesis and Reactions