Silica-Grafted Basic Amino Acids as Environmentally Benign Catalysts for the Solventless Synthesis of Cyclic Carbonates from Epoxides and CO2 under Metal-Free and Halide-Free Conditions

Abdol Reza Hajipour; Yasaman Heidari; Gholamreza Kozehgary

doi:10.1055/s-0035-1561309

Synlett, Table of Contents

Synlett 2016; 27(06): 929-933
DOI: 10.1055/s-0035-1561309

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Silica-Grafted Basic Amino Acids as Environmentally Benign Catalysts for the Solventless Synthesis of Cyclic Carbonates from Epoxides and CO₂ under Metal-Free and Halide-Free Conditions

Abdol Reza Hajipour*

^aPharmaceutical Research Laboratory, Department of Chemistry, Isfahan University of Technology, Isfahan 84156, Iran Email: haji@cc.iut.ac.ir

^bDepartment of Neuroscience, University of Wisconsin, Medical School, 1300 University Avenue, Madison, WI 53706-1532, USA

,

Yasaman Heidari

^aPharmaceutical Research Laboratory, Department of Chemistry, Isfahan University of Technology, Isfahan 84156, Iran Email: haji@cc.iut.ac.ir

,

Gholamreza Kozehgary

^cDepartment of Chemistry, Shahid Beheshti University, G. C., Evin, Tehran 1983963113, Iran

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Abstract

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Abstract

A series of basic amino acids immobilized onto solid supports that can play cooperative roles was developed and applied as environmentally benign catalytic systems for the solventless synthesis of cyclic carbonates from epoxides and carbon dioxide under metal-free and halide-free conditions. The highest yield of styrene carbonate was achieved with silica supported l-histidine, associated with the acidic nature of silica: Si–OH groups on the silica surface act as a weak acid to activate the epoxide for the synergetic effect with the basic amino acid. The influence of various reaction parameters on catalytic activity was investigated. Moreover, the catalyst exhibited good recyclability.

Key words

silica-supported amino acids - carbon dioxide - cyclic carbonate - epoxide - cycloaddition

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