Abstract
Supported ionic liquid-like phases (SILLPs) containing Rose Bengal (RB) units are used to develop organocatalytic systems for the cycloaddition of CO2 to epoxides. The activity of the supported RB fragments can be fine-tuned by controlling the nature of the SILLPs (i.e., substitution at the imidazolium ring, cross-linking degree of the polymeric matrix, loading, etc.). Such a catalytic system prepared from cheap, simple, and commercially available components provides high activity and stability, with no decay in activity for at least 10 days of continuous use under flow conditions.
Highlights
Cyclic carbonates have emerged as compounds of interest for many applications including their use as electrolytes in Li-ion batteries, as polar aprotic solvents for the synthesis of fine chemicals, or as monomers in the preparation of polycarbonates and polyurethanes.[1−4] enormous progress has been made in the past few years to improve their synthetic access
This study shows how a simple organocatalyst based on Rose Bengal (RB) immobilized onto supported ionic liquid-like phases (SILLPs) can be used to efficiently transform epoxides into the corresponding cyclic carbonates in the presence of CO2 with relevant turn over
The polymeric supported ionic liquidlike phases (SILLPs) considered in this work were prepared from commercially available Merrifield resins
Summary
Cyclic carbonates have emerged as compounds of interest for many applications including their use as electrolytes in Li-ion batteries, as polar aprotic solvents for the synthesis of fine chemicals, or as monomers in the preparation of polycarbonates and polyurethanes.[1−4] enormous progress has been made in the past few years to improve their synthetic access. It must be noted that this recovered RB-SILLP was able to act as an efficient catalyst for a new reaction under similar batch conditions In view of these results, the preparation of the zwitterionic NHC−CO2 polymer (31) was assayed following already reported synthetic methods involving deprotonation of the C2 acid proton of the imidazolium in the presence of a base followed by reaction with CO2.51 This resin (31) provided the cyclic adduct 29 with a conversion of ca. The productivity of this system was 1.129 gcyclocarbonate/(gcatalyst h), which is among the higher productivities reported so far under continuous flow conditions (Table S2)
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