Oxidative carbonylation: Difference between revisions
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Oxidative carbonylation is a class of reactions that use carbon monoxide in combination with an oxidant to generate esters. These transformations utilize transition metal complexes as homogeneous catalysts.[1] Many of these reactions employ palladium catalysts. Mechanistically, these reactions resemble the Wacker process.
Illustrative oxidative carbonylations
Conversion of alkenes into homologated esters:
- RCH=CH2 + CO + 1/2 O2 + MeOH → RCH=CHCO2Me + H2O
These reactions are assumed to proceed by the insertion of the alkene into a metallacarboxylic ester (LnPd-CO2Me) followed by beta-hydride elimination.
Conversion of methanol to dimethylcarbonate:
- CO + 1/2 O2 + 2 MeOH → (MeO)2CO + H2O
This method competes with phosgenation.
References
- ^ "Oxidative Carbonylation Reactions In Transition Metal Catalyzed Carbonylation Reactions: Carbonylative Activation of C-X Bonds". Transition Metal Catalyzed Carbonylation Reactions: Carbonylative Activation of C-X Bonds. Berlin, Heidelberg: Springer. 2013. doi:10.1007/978-3-642-39016-6_8.
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