Flow Microreactor Technology for Taming Highly Reactive Chloroiodomethyllithium Carbenoid: Direct and Chemoselective Synthesis of α-Chloroaldehydes
Pantaleo Musci, Marco Colella, Alessandra Sivo, Giuseppe Romanazzi, Renzo Luisi, Leonardo Degennaro
Abstract
A straightforward flow synthesis of α-chloro aldehydes has been developed. The strategy involves, for the first time, the thermal unstable chloroiodomethyllithium carbenoid and carbonyl compounds. A batch versus flow comparative study showcases the superb capability of flow technology in prolonging the lifetime of the lithiated carbenoid, even at -20 °C. Remarkably, the high chemoselectivity realized in flow allowed for preparing polyfunctionalized α-chloro aldehydes not easily accessible with traditional batch procedures.
Topics & Concepts
CarbenoidChemoselectivityMicroreactorChemistryFlow chemistryCombinatorial chemistryFlow (mathematics)Continuous flowCatalysisOrganic chemistryBiochemical engineeringRhodiumEngineeringGeometryMathematicsInnovative Microfluidic and Catalytic Techniques InnovationNanomaterials for catalytic reactionsAsymmetric Hydrogenation and Catalysis