Copper(I)‐Catalyzed Four‐Component Coupling Using Renewable Building Blocks of CO2 and Biomass‐Based Aldehydes

Both carbon dioxide‐ (CO2) and biomass‐based molecules have recently been regarded as renewable, abundant, environmentally benign, and attractive carbon feedstocks for organic synthesis. Therefore, a mild and efficient method for the synthesis of 1,3‐oxazolidin‐2‐ones was developed through a “green”...

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Veröffentlicht in:European journal of organic chemistry 2018-06, Vol.2018 (24), p.3105-3113
Hauptverfasser: Wu, Qiumin, Chen, Jinzhu, Guo, Xuhong, Xu, Yisheng
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Sprache:eng
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Zusammenfassung:Both carbon dioxide‐ (CO2) and biomass‐based molecules have recently been regarded as renewable, abundant, environmentally benign, and attractive carbon feedstocks for organic synthesis. Therefore, a mild and efficient method for the synthesis of 1,3‐oxazolidin‐2‐ones was developed through a “green” four‐component coupling reaction by using CO2, biomass‐based aldehydes such as furfural and 5‐hydroxymethylfurfural (HMF), terminal aromatic alkynes, and primary aliphatic amines with copper iodide as a catalyst. 24 Furyl‐substituted 1,3‐oxazolidin‐2‐ones were obtained in 29–84 % yield from the four‐component coupling reaction. Moreover, the coupling reaction was applicable to the syntheses of furyl‐containing bisoxazolidinone and polyoxazolidinone under mild conditions. Furyl‐containing oxazolidinones, bisoxazolidinone, and polyoxazolidinone were obtained by copper‐promoted four‐component coupling using renewable building blocks of CO2 and biomass‐based aldehydes.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.201800461