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Cited by 314

The DOI matches its Crossref record; 73 of the 73 references it cites were found in a registry or an index.

Fast CO2 Sequestration, Activation, and Catalytic Transformation Using N-Heterocyclic Olefins

Wang, Yan-Bo, Wang, Yi-Ming, Zhang, Wen-Zhen, Lu, Xiao-Bing·2013·Journal of the American Chemical Society
DOI 10.1021/ja405114e
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Abstract

N-Heterocyclic Olefin (NHO) with high electronegativity at the terminal carbon atom was found to show a strong tendency for CO2 sequestration, affording a CO2 adduct (NHO-CO2). X-ray single crystal analysis revealed the bent geometry of the binding CO2 in the NHO-CO2 adducts with an O-C-O angle of 127.7-129.9°, dependent on the substitute groups of N-heterocyclic ring. The length of the C(carboxylate)-C(NHO) bond is in the range of 1.55-1.57 Å, significantly longer than that of the C(carboxylate)-C(NHC) bond (1.52-1.53 Å) of the previously reported NHC-CO2 adducts. The FTIR study by monitoring the ν(CO2) region of transmittance change demonstrated that the decarboxylation of NHO-CO2 adducts is easier than that of the corresponding NHC-CO2 adducts. Notably, the NHO-CO2 adducts were found to be highly active in catalyzing the carboxylative cyclization of CO2 and propargylic alcohols at mild conditions (even at ambient temperature and 0.1 MPa CO2 pressure), selectively giving α-alkylidene cyclic carbonates in good yields. The catalytic activity is about 10-200 times that of the corresponding NHC-CO2 adducts at the same conditions. Two reaction paths regarding the hydrogen at the alkenyl position of cyclic carbonates coming from substrate (path A) or both substrate and catalyst (path B) were proposed on the basis of deuterium labeling experiments. The high activity of NHO-CO2 adduct was tentatively ascribed to its low stability for easily releasing the CO2 moiety and/or the desired product, a possible rate-limiting step in the catalytic cycle.

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Metadata

Authors
Wang, Y.-B., Wang, Y.-M., Zhang, W.-Z., & Lu, X.-B.
Venue
Journal of the American Chemical Society
Publisher
American Chemical Society (ACS)
Published
2013-07-31
Volume
135
Issue
32
Pages
11996-12003
ISSN
  • 0002-7863 (ISSN-L)
  • 1520-5126
DOI
10.1021/ja405114e
OpenAlex
W1990020617
Cited by
314
References
73
FWCI
12.40
Type
journal article
Language
en
Open access
closed

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