Silacarboxylic Acids as Efficient Carbon Monoxide Releasing Molecules: Synthesis and Application in Palladium-Catalyzed Carbonylation Reactions

详细信息    查看全文

• 作者：Stig D. Friis ; Rolf H. Taaning ; Anders T. Lindhardt ; Troels Skrydstrup
• 刊名：Journal of the American Chemical Society
• 出版年：2011
• 出版时间：November 16, 2011
• 年：2011
• 卷：133
• 期：45
• 页码：18114-18117
• 全文大小：772K
• 年卷期：v.133,no.45(November 16, 2011)
• ISSN：1520-5126

文摘

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 MePh₂SiCO₂H 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 MePh₂Si¹³CO₂H and its application in carbonyl labeling of two bioactive compounds was demonstrated.