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

被引：260

作者：

Friis, Stig D.

Taaning, Rolf H.

Lindhardt, Anders T.

Skrydstrup, Troels ^{[1
]}

机构：

[1] Aarhus Univ, Ctr Insoluble Prot Struct inSPIN, Dept Chem, Langelandsgade 140, DK-8000 Aarhus C, Denmark

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2011年 / 133卷 / 45期

基金：

新加坡国家研究基金会;

关键词：

EX-SITU; AMINOCARBONYLATION; REARRANGEMENTS; ORGANOSILICON; PRESSURE;

D O I：

10.1021/ja208652n

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

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 (MePh2SiCO2H)-C-13 and its application in carbonyl labeling of two bioactive compounds was demonstrated.

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收藏

页码：18114 / 18117

页数：4

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