Abstract
A bifunctional and recyclable organocatalyst shows excellent performance in the formation of cyclic carbonates from both terminal and internal epoxides.
Highlights
We previously reported the successful immobilization of pyrogallol onto a bifunctional polystyrene support and application as a recyclable catalyst for cyclic carbonate synthesis
We present a simple and effective approach towards the preparation of modular bifunctional catalysts for cyclic organic carbonates (COCs) synthesis, the immobilization onto a polystyrene support and the recycling features of this hetero
The intermediates 5–11 were treated with strong aqueous acids (HCl, HBr) to afford the ring-opened benzyl ammonium functionalized resorcinarenes 12–19. The latter compounds were fully characterized by 1H/13C NMR, IR and elemental analysis prior to their use in the catalytic studies
Summary
Carbon dioxide (CO2) is an abundant waste material that may be recycled using effective catalysis technologies.1 Key to CO2 conversion is the use of high-energy reactants that provide a thermodynamic driving force, and historically epoxides have been popular coupling partners to afford cyclic organic carbonates (COCs).2 These heterocyclic structures find many useful applications representing precursors for polymeric carbonates,3 being green solvents4 and offering new opportunities in synthetic chemistry.5 The “fixation” of CO2 into COCs has advanced tremendously over the years with a prominent role for (transition) metal-based catalysts.6 The use of efficient metal catalysis has allowed, inter alia, the resolution of challenging conversions of CO2 with oxetanes,7 and disubstituted8 and even trisubstituted oxiranes.9In contrast, organocatalysts have only recently emerged as potential sustainable alternatives to metal-based catalyst systems,10 though the vast majority of the cases still require the assistance of co-catalysts, solvents and/or elevated temperatures (>100 °C). We previously reported the successful immobilization of pyrogallol onto a bifunctional polystyrene support and application as a recyclable catalyst for cyclic carbonate synthesis.16 Inspired by our former results, we imagined that the immobilization of amine-functionalized resorcinarenes would offer powerful bifunctional catalysts (Fig. 1c) amplifying their potential towards metal-free, recyclable systems for COC formation.
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