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Realizing Metal-Free Carbene-Catalyzed Carbonylation Reactions with CO

Authors :
Max M. Hansmann
Eder Tomás-Mendivil
Jesse L Peltier
Rodolphe Jazzar
Daniel R. Tolentino
Guy Bertrand
University of California [San Diego] (UC San Diego)
University of California
Source :
Journal of the American Chemical Society, Journal of the American Chemical Society, American Chemical Society, 2020, 142 (43), pp.18336-18340. ⟨10.1021/jacs.0c09938⟩
Publication Year :
2020

Abstract

International audience; 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 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 ortho-quinone into a cyclic carbonate. These findings pave the way for the discovery of metal-free catalyzed carbonylation reactions.

Details

ISSN :
15205126 and 00027863
Volume :
142
Issue :
43
Database :
OpenAIRE
Journal :
Journal of the American Chemical Society
Accession number :
edsair.doi.dedup.....4473856ac4ee31f423769abc07fefbf7
Full Text :
https://doi.org/10.1021/jacs.0c09938⟩