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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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| Published in: | Journal of the American Chemical Society 2020-10, Vol.142 (43), p.18336-18340 |
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| Main Authors: | , , , , , |
| Format: | Article |
| Language: | English |
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| cited_by | cdi_FETCH-LOGICAL-a423t-fa8ee5ad2e689bd6e8af3fec8122518058cf9eb788dac5d93c6a04b444111a313 |
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| cites | cdi_FETCH-LOGICAL-a423t-fa8ee5ad2e689bd6e8af3fec8122518058cf9eb788dac5d93c6a04b444111a313 |
| container_end_page | 18340 |
| container_issue | 43 |
| container_start_page | 18336 |
| container_title | Journal of the American Chemical Society |
| container_volume | 142 |
| creator | Peltier, Jesse L Tomás-Mendivil, Eder Tolentino, Daniel R Hansmann, Max M Jazzar, Rodolphe Bertrand, Guy |
| description | 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. |
| doi_str_mv | 10.1021/jacs.0c09938 |
| format | article |
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| ispartof | Journal of the American Chemical Society, 2020-10, Vol.142 (43), p.18336-18340 |
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| language | eng |
| recordid | cdi_osti_scitechconnect_1773888 |
| source | American Chemical Society:Jisc Collections:American Chemical Society Read & Publish Agreement 2022-2024 (Reading list) |
| subjects | Carbonylation Catalysis Chemical Sciences Inorganic carbon compounds INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY Organic chemistry Oxides Reductive elimination Transition metals |
| title | Realizing Metal-Free Carbene-Catalyzed Carbonylation Reactions with CO |
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