Cyclic (Alkyl)(amino)carbenes: Synthesis of Iminium Precursors and Structural Properties

Cyclic (Alkyl)(amino)carbenes: Synthesis of Iminium Precursors and Structural Properties

Using readily available preallylated aldehydes, we report a simple and divergent synthesis of cyclic (alkyl)­(amino)­carbene (CAAC) iminium precursors. Using a combination of crystallographic data and steric maps, we further elaborate on the specific steric properties of CAAC ligands with respect to...

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Bibliographic Details
Published in:Journal of organic chemistry Vol. 87; no. 5; pp. 3511 - 3518
Main Authors: Vermersch, François, Oliveira, Luana, Hunter, Joseph, Soleilhavoup, Michele, Jazzar, Rodolphe, Bertrand, Guy
Format: Journal Article
Language:English
Published: United States American Chemical Society 04-03-2022
Subjects:
Aldehydes
Chemical Sciences
Granular materials
INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
Ligands
Lipids
Methane - analogs & derivatives
Methane - chemistry
Mixtures
Nuclear magnetic resonance spectroscopy
Organic chemistry
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Summary:Using readily available preallylated aldehydes, we report a simple and divergent synthesis of cyclic (alkyl)­(amino)­carbene (CAAC) iminium precursors. Using a combination of crystallographic data and steric maps, we further elaborate on the specific steric properties of CAAC ligands with respect to state-of-the-art phosphine and carbene ligands.
Bibliography:ObjectType-Article-1
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content type line 23
USDOE Office of Science (SC), Basic Energy Sciences (BES)
SC0009376; ANR-20-CE07-0000-cResolu
French National Research Agency (ANR)
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.1c03075