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Development of Suitable Hydrogen Bond Donor (HBD) Catalysts for the Synthesis of Cyclic Carbonates and Dithiocarbonates from Epoxide

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Abstract

Novel ketimine derivatives have been designed, synthesized and employed as a Hydrogen Bond Donor (HBD) catalyst for the successful incorporation of CO2 in epoxides en route to the synthesis of cyclic carbonates. The catalytic activity was observed to be directly correlated with the structural features of such ketimine derivatives, where the accountability of the protocol governs by the extent of non-covalent interactions. As such, the accessibility of the “H(s)” present in the catalyst is the primary criteria for the formation of feasible H-bond(s) to activate the substrate. These characteristic properties have been observed for the catalytic activities of the different ketimine derivatives. We have found that the positions of the H’s plays a crucial role for the formation of single or dual H-bonds with the substrate epoxides, which actually dictates the catalytic efficiency. In our domino ring opening followed by cyclization protocol, the HBD catalyst has been used along with a co-catalyst, tetrabutyl ammonium iodide (TBAI). The iodide ion acts as a nucleophile to open the epoxide ring, followed by the cyclization reaction takes place with CO2. The role of the HBD catalyst is found to activate the ring opening step as well as to stabilize the oxyanion intermediate, which forms after the O–C bond formation with CO2. The methodology has been optimized in a sustainable solvent free condition and generalized to obtain a variety of cyclic carbonates in good to excellent yields. Similarly, this strategy has been further extended for the synthesis of cyclic dithiocarbonate by the reaction of epoxide with carbon-di-sulphide (CS2) as an electrophile under the same catalytic condition. In this case the corresponding products were obtained as a mixture of regioisomer.

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Acknowledgements

Science and Engineering Research Board (SERB) (ECR/2017/000966) Govt. of India, is highly acknowledged for funding and Visvesvaraya National Institute of Technology (VNIT) Nagpur for providing the infrastructure. SR and KD are extremely thankful to SERB, DST and VNIT Nagpur for their research fellowships.

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Science and Engineering Research Board, ECR/2017/000966.

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  1. Shilpa Roy and Koushik Das have contributed equally to this work.

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  1. Laboratory of Organo Catalysis and Synthesis, Department of Chemistry, Visvesvaraya National Institute of Technology (VNIT), Nagpur, Maharashtra, 440010, India

    Shilpa Roy, Koushik Das & Sandipan Halder

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  1. Shilpa Roy
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Roy, S., Das, K. & Halder, S. Development of Suitable Hydrogen Bond Donor (HBD) Catalysts for the Synthesis of Cyclic Carbonates and Dithiocarbonates from Epoxide. Catal Lett 154, 2243–2254 (2024). https://doi.org/10.1007/s10562-023-04422-y

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