Atmospheric Pressure of CO<sub>2</sub> as Protecting Reagent and Reactant: Efficient Synthesis of Oxazolidin‐2‐ones with Carbamate Salts, Aldehydes and Alkynes

Bing Yu, Weiqi Liu, Wei Li, Shanshan Wang, Jie Cao, Changwen Hu

Advanced Synthesis & Catalysis · 2015 · 48 citations · 62 references

Concepts

Abstract

Abstract Carbon dioxide (CO 2 ) has been wildly employed as an environmentally benign C 1 resource for organic synthesis in the recent years. The capture of CO 2 with primary amines easily provides the corresponding carbamate salts. We described herein that carbamate salts are a useful reactant for the synthesis of oxazolidin‐2‐ones via the reaction with aromatic aldehydes and aromatic terminal alkynes. A variety of oxazolidin‐2‐ones with different functional groups were synthesized in 68–91% yields with only a 5 mol% amount of CuI as catalyst. It was found that the synergetic effect of iodide is important for the transformation. Notable, the captured CO 2 serves not only as a protecting reagent for electron‐rich primary amine to avoid catalyst poisoning, but also as a reactant for the construction of oxazolidin‐2‐ones. magnified image

References

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