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

doi:10.1021/acssuschemeng.7b01650

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 journal › Article › peer-review

159 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 language	English (US)
Pages (from-to)	6392-6397
Number of pages	6
Journal	ACS Sustainable Chemistry & Engineering
Volume	5
Issue number	8
DOIs	https://doi.org/10.1021/acssuschemeng.7b01650
State	Published - 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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https://repository.kaust.edu.sa/bitstream/10754/625212/1/acssuschemeng.7b01650.pdf

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

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.",

author = "Sunatda Arayachukiat and Chutima Kongtes and Alexander Barthel and Vummaleti, {Sai V. C.} and Albert Poater and Sippakorn Wannakao and Luigi Cavallo and Valerio D{\textquoteright}Elia",

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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doi = "10.1021/acssuschemeng.7b01650",

language = "English (US)",

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AU - Arayachukiat, Sunatda

AU - Kongtes, Chutima

AU - Barthel, Alexander

AU - Vummaleti, Sai V. C.

AU - Poater, Albert

AU - Wannakao, Sippakorn

AU - Cavallo, Luigi

AU - D’Elia, Valerio

N1 - 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.

PY - 2017/7/18

Y1 - 2017/7/18

N2 - 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.

AB - 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.

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JO - ACS Sustainable Chemistry & Engineering

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IS - 8

ER -

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

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