CO 2 Adducts of Carbodicarbenes: Robust and Versatile Organocatalysts for Chemical Transformation of Carbon Dioxide into Heterocyclic Compounds

Four CO 2 adducts of carbodicarbenes (CDCs) were first synthesized and structurally characterized by means of NMR spectroscopy, high‐resolution mass spectrometry, and FTIR spectroscopy. The introduction of 13 C‐labelled CO 2 confirmed the formation of the corresponding carboxylated species. Thermogr...

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Bibliographic Details
Published in:ChemCatChem 2018-06, Vol.10 (12), p.2686-2692
Main Authors: Liu, An‐Hua, Dang, Ya‐Li, Zhou, Hui, Zhang, Jin‐Ju, Lu, Xiao‐Bing
Format: Article
Language:English
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Summary:Four CO 2 adducts of carbodicarbenes (CDCs) were first synthesized and structurally characterized by means of NMR spectroscopy, high‐resolution mass spectrometry, and FTIR spectroscopy. The introduction of 13 C‐labelled CO 2 confirmed the formation of the corresponding carboxylated species. Thermogravimetric analysis (TGA) provided detailed information on their thermal decarboxylation processes. The novel CDC–CO 2 adducts were subsequently applied as robust and versatile organocatalysts for the carboxylative cyclization of CO 2 with aziridines, epoxides, or propargylic alcohols, affording 2‐oxazolidinones and cyclic carbonates in good to excellent yields (51–99 %) and high functional group tolerance. TGA results together with control experiments indicate that the in situ formed free CDC by decarboxylation of the corresponding CDC–CO 2 adducts plays the key role to activate the substrates by its strong Lewis basicity.
ISSN:1867-3880
1867-3899
DOI:10.1002/cctc.201800148