Realizing Metal-Free Carbene-Catalyzed Carbonylation Reactions with CO

Many organic and main-group compounds, usually acids or bases, can accelerate chemical reactions when used in substoichiometric quantities, a process known as organocatalysis. In marked contrast, very few of these compounds are able to activate carbon monoxide, and until now, none of them could cata...

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Bibliographic Details
Published in:Journal of the American Chemical Society 2020-10, Vol.142 (43), p.18336-18340
Main Authors: Peltier, Jesse L, Tomás-Mendivil, Eder, Tolentino, Daniel R, Hansmann, Max M, Jazzar, Rodolphe, Bertrand, Guy
Format: Article
Language:English
Subjects:
Carbonylation
Catalysis
Chemical Sciences
Inorganic carbon compounds
INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
Organic chemistry
Oxides
Reductive elimination
Transition metals
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Summary:Many organic and main-group compounds, usually acids or bases, can accelerate chemical reactions when used in substoichiometric quantities, a process known as organocatalysis. In marked contrast, very few of these compounds are able to activate carbon monoxide, and until now, none of them could catalyze its chemical transformation, a classical task for transition metals. Herein we report that a stable singlet ambiphilic carbene activates CO and catalytically promotes the carbonylation of an o-quinone into a cyclic carbonate. These findings pave the way for the discovery of metal-free catalyzed carbonylation reactions.
ISSN:0002-7863
1520-5126
DOI:10.1021/jacs.0c09938