Ascorbic acid as a bifunctional hydrogen bond donor for the synthesis of cyclic carbonates from CO2 under ambient conditions

Sunatda Arayachukiat, Chutima Kongtes, Alexander Barthel, Sai V. C. Vummaleti, Albert Poater, Sippakorn Wannakao, Luigi Cavallo, Valerio D’Elia

Research output: Contribution to journalArticlepeer-review

153 Scopus citations

Abstract

Readily available ascorbic acid was discovered as an environmentally benign hydrogen bond donor (HBD) for the synthe-sis of cyclic organic carbonates from CO2 and epoxides in the presence of nucleophilic co-catalysts. The ascorbic acid/TBAI (TBAI: tetrabutylammonium iodide) binary system could be applied for the cycloaddition of CO2 to various epoxides under ambient or mild conditions. DFT calculations and catalysis experiments revealed an intriguing bifunctional mechanism in the step of CO2 insertion involving different hydroxyl moieties (enediol, ethyldiol) of the ascorbic acid scaffold.
Original languageEnglish (US)
Pages (from-to)6392-6397
Number of pages6
JournalACS Sustainable Chemistry & Engineering
Volume5
Issue number8
DOIs
StatePublished - Jul 18 2017

Bibliographical note

KAUST Repository Item: Exported on 2020-10-01
Acknowledgements: A.P. thanks the Spanish MINECO for the project CTQ2014-59832-JIN. V.D.E. thanks the Thailand Research Fund (Grant No. RSA6080059) for funding this research. This publication is based upon work supported by the King Abdullah University of Science and Technology (KAUST). S.A. acknowledges financial support through postdoctoral fellowship from the Vidyasirimedhi Institute of Science and Technology.

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