Ambient carboxylation on a supported reversible CO2 carrier: ketone to β-keto ester

被引:31
作者
Beckman, Eric J. [1 ]
Munshi, Pradip [1 ,2 ,3 ]
机构
[1] Univ Pittsburgh, Dept Chem Engn, Pittsburgh, PA 15261 USA
[2] Rubamin Labs Ltd, Vadodara 391323, Gujarat, India
[3] Reliance Ind Ltd, Res Ctr, Vadodara 391346, Gujarat, India
关键词
ACTIVE METHYLENE-COMPOUNDS; CARBON-DIOXIDE; GREEN CHEMISTRY; VINYL CHLORIDE; COMPLEXES; SOLVENT; RELEASE; SPECTRA; REAGENT; TOLUENE;
D O I
10.1039/c0gc00704h
中图分类号
O6 [化学];
学科分类号
070301 [无机化学];
摘要
A reversible CO2 carrier (RCC) has been developed to perform carboxylation of ketone to beta-ketoester under ambient CO2 pressure and temperature. RCC has been synthesized by immobilizing 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) on methylhydrosiloxane support and reacting with CO2 with 100% degree of functionalisation. RCC is found to be recyclable and shows retention of activity in 5 recycles. CO2 absorption under ambient temperature and desorption at 120 degrees C renders the material suitable for carrying out carboxylation reactions at 25 degrees C with excellent yields. The yield of the reaction can reach up to 100% with TON 200 in 4 h. The extent of the reaction primarily depends upon enol content of the substrate. beta-Ketoacid produced during the reaction can be isolated and converted to its corresponding methyl ester derivative by reacting with methyl iodide.
引用
收藏
页码:376 / 383
页数:8
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