Lewis Basic Salt-Promoted Organosilane Coupling Reactions with Aromatic Electrophiles
Tyler W. Reidl, Jeffrey S. Bandar
Abstract
Lewis basic salts promote benzyltrimethylsilane coupling with (hetero)aryl nitriles, sulfones, and chlorides as a new route to 1,1-diarylalkanes. This method combines the substrate modularity and selectivity characteristic of cross-coupling with the practicality of a base-promoted protocol. In addition, a Lewis base strategy enables a complementary scope to existing methods, employs stable and easily prepared organosilanes, and achieves selective arylation in the presence of acidic functional groups. The utility of this method is demonstrated by the synthesis of pharmaceutical analogues and its use in multicomponent reactions.
Topics & Concepts
ChemistryLewis acids and basesElectrophileCombinatorial chemistryArylSalt (chemistry)Substrate (aquarium)SelectivityModularity (biology)Base (topology)Scope (computer science)Coupling (piping)Organic chemistryCatalysisAlkylGeneticsEngineeringMechanical engineeringBiologyGeologyOceanographyComputer scienceMathematicsMathematical analysisProgramming languageSulfur-Based Synthesis TechniquesCatalytic Cross-Coupling ReactionsCatalytic C–H Functionalization Methods