Copper-Catalyzed Direct Carbonylation of Carbenes toward the Synthesis of Propanedioic Acid Derivatives

Abstract

Carbenes are highly active reaction intermediates, which can be used as reaction precursors to modify organisms, drugs, and material molecules. In this work, we realized a new cheap metal-catalyzed carbonylation of carbene to give propanedioic acid derivatives. With copper salt as the catalyst, synthetically important malonates and related compounds were produced in good yields under mild reaction conditions.

On the Question of Uncatalyzed CO Insertion into a Hydrazone Double Bond: A Comparative Study Using Different CO Sources and Substrates

“…Carbonylation occupies a very special place in organic synthesis and represents some of the most useful reactions to enable access to a wide range of carbonyl containing intermediates. , All known carbonylation reactions require catalysis by a transition-metal complex, including various complexes of ruthenium, rhodium, iron, palladium, cobalt, and copper . Interestingly, palladium-mediated carbonylation has been very cleverly used by Chang and colleagues for developing fluorescent probes for detecting carbon monoxide (CO) in biological settings (Scheme A) .…”

“… 1 , 2 All known carbonylation reactions require catalysis by a transition-metal complex, including various complexes of ruthenium, rhodium, 3 iron, 4 palladium, 5 cobalt, 6 and copper. 7 Interestingly, palladium-mediated carbonylation has been very cleverly used by Chang and colleagues for developing fluorescent probes for detecting carbon monoxide (CO) in biological settings ( Scheme 1 A). 8 One can safely say that this publication by Michel, Lippert, and Chang started a wave of work on designing new small-molecule fluorescent probes for CO with various designs, 9 including the use of Pd-catalyzed carbonylation and Pd-mediated deallylation for fluorophore activation in CO detection ( Table S2 ).…”