A Metal‐Free Synthesis of <i>N</i>‐Aryl Oxazolidin‐2‐Ones by the One‐Pot Reaction of Carbon Dioxide with <i>N</i>‐Aryl Aziridines
Paolo Sonzini, Caterina Damiano, Daniela Intrieri, Gabriele Manca, Emma Gallo
Abstract
Abstract The cost‐effective TPPH 2 /TBACl‐catalyzed (TPPH 2 =dianion of tetraphenyl porphyrin; TBACl=tetrabutyl ammonium chloride) carbon dioxide cycloaddition to N ‐aryl aziridines was successful in synthesizing N ‐aryl oxazolidin‐2‐ones. A catalytic tandem reaction was also developed, in which N ‐aryl aziridines were initially synthesized and then reacted with carbon dioxide without being purified. The procedure occurred with a very high atom economy, molecular nitrogen being the only by‐product of the entire tandem process. In addition, the mechanism of catalytic cycle was investigated by DFT calculations. magnified image
Topics & Concepts
ChemistryArylCatalysisTandemCycloadditionCarbon dioxideAtom economyMetalOrganic chemistryMedicinal chemistryCombinatorial chemistryComposite materialMaterials scienceAlkylCarbon dioxide utilization in catalysisCO2 Reduction Techniques and CatalystsSynthesis and Catalytic Reactions