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.
A Metal-Free Synthesis of N -Aryl Oxazolidin-2-ones by the One-Pot Reaction of Carbon Dioxide with N -Aryl Aziridines
Gabriele Manca;
2020
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.| File | Dimensione | Formato | |
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Adv. Synth. Catal. 2020, 362, 2961 – 2969.pdf
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proof_Advanced Synthesis & Catalysis_2020.pdf
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Descrizione: "This is the peer reviewed version of the following article: P. Sonzini, C. Damiano, D. Intrieri, G. Manca, E. Gallo, Adv. Synth. Catal. 2020, 362, 2961, which has been published in final form at https://doi.org/10.1002/adsc.202000175. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Use of Self-Archived Versions. This article may not be enhanced, enriched or otherwise transformed into a derivative work, without express permission from Wiley or by statutory rights under applicable legislation. Copyright notices must not be removed, obscured or modified. The article must be linked to Wiley’s version of record on Wiley Online Library and any embedding, framing or otherwise making available the article or pages thereof by third parties from platforms, services and websites other than Wiley Online Library must be prohibited."
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