A Metal‐Free Synthesis of N‐Aryl Oxazolidin‐2‐Ones by the One‐Pot Reaction of Carbon Dioxide with N‐Aryl Aziridines. Issue 14 (21st June 2020)

• Record Type: Journal Article
• Authors: Sonzini, Paolo; Damiano, Caterina; Intrieri, Daniela; Manca, Gabriele; Gallo, Emma
• Is Part Of: Advanced synthesis & catalysis. Volume 362:Issue 14(2020)
• Page Start: 2961
• Page End: 2969
• Publication Date: 2020-06-21
• Subjects: N-aryl oxazolidin-2-one -- Carbon dioxide -- Aziridine -- Porphyrin -- DFT study; Catalysis -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Chemistry -- Periodicals; Chemistry, Technical -- Periodicals; Chemistry -- Periodicals; Catalysis -- Periodicals; Technology, Pharmaceutical -- Periodicals; 547.2
• DOI: 10.1002/adsc.202000175
• Languages: English
• ISSNs: 1615-4150

Abstract

Abstract: The cost‐effective TPPH2 /TBACl‐catalyzed (TPPH2 =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. Abstract :