Silacarboxylic acids as efficient carbon monoxide releasing molecules: synthesis and application in palladium-catalyzed carbonylation reactions.
Silacarboxylic acids have been demonstrated to be easy to handle, air-stable carbon monoxide precursors. Different silacarboxylic acids were synthesized from the corresponding chlorosilanes and carbon dioxide, and their decarbonylation, upon treatment with an array of activators, was evaluated. The release of CO from crystalline MePh(2)SiCO(2)H proved to be highly efficient, and it was successfully applied in a selection of palladium-catalyzed carbonylative couplings using near-stoichiometric quantities of carbon monoxide precursor. Finally, the synthesis of MePh(2)Si(13)CO(2)H and its application in carbonyl labeling of two bioactive compounds was demonstrated.
Center for Insoluble Protein Structures (inSPIN), Department of Chemistry, Aarhus University, Langelandsgade 140, 8000 Aarhus C, Denmark.
Stig D
SD
Friis
Rolf H
RH
Taaning
Anders T
AT
Lindhardt
Troels
T
Skrydstrup
D002248:Carbon Monoxide / Q000737:chemistry*; D002264:Carboxylic Acids / Q000138:chemical synthesis / Q000737:chemistry*; D002384:Catalysis; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry*; D012821:Silanes / Q000138:chemical synthesis / Q000737:chemistry*
D002264:Carboxylic Acids; D012821:Silanes; D010165:Palladium; D002248:Carbon Monoxide