Electrosynthesis of enantiomerically pure cyclic carbonates from CO 2 and chiral epoxides

Yan Xiao; Bao Li Chen; Heng Pan Yang; Huan Wang; Jia Xing Lu

doi:10.1016/j.elecom.2014.03.012

Electrosynthesis of enantiomerically pure cyclic carbonates from CO ₂ and chiral epoxides

Yan Xiao, Bao Li Chen, Heng Pan Yang, Huan Wang^*, Jia Xing Lu

^*Corresponding author for this work

School of Chemistry and Molecular Engineering

East China Normal University

Research output: Contribution to journal › Article › peer-review

27 Scopus citations

Abstract

In this paper, the one-step synthesis of enantiomerically pure cyclic carbonates has been developed by electrolyzing the chiral epoxides and CO ₂ (0.1 MPa, rt) in an undivided cell with a 316 stainless steel (SS) cathode and a Mg sacrificial anode containing TEAI-MeCN as supporting electrolyte and solvent with a constant current. To deeply understand this reaction, the effects of various synthesis conditions were investigated using R-styrene oxide as the model compound. Under the optimized conditions, the maximum conversion is 67% with 96% selectivity and 98.8% ee value for R-styrene carbonate. Finally, the reaction mechanism has been proposed by comparative electrolysis and DFT calculation.

Original language	English
Pages (from-to)	71-74
Number of pages	4
Journal	Electrochemistry Communications
Volume	43
DOIs	https://doi.org/10.1016/j.elecom.2014.03.012
State	Published - Jun 2014

Keywords

CO
Chiral epoxides
Cyclic carbonates
Electrosynthesis

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10.1016/j.elecom.2014.03.012

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title = "Electrosynthesis of enantiomerically pure cyclic carbonates from CO 2 and chiral epoxides",

abstract = "In this paper, the one-step synthesis of enantiomerically pure cyclic carbonates has been developed by electrolyzing the chiral epoxides and CO 2 (0.1 MPa, rt) in an undivided cell with a 316 stainless steel (SS) cathode and a Mg sacrificial anode containing TEAI-MeCN as supporting electrolyte and solvent with a constant current. To deeply understand this reaction, the effects of various synthesis conditions were investigated using R-styrene oxide as the model compound. Under the optimized conditions, the maximum conversion is 67\% with 96\% selectivity and 98.8\% ee value for R-styrene carbonate. Finally, the reaction mechanism has been proposed by comparative electrolysis and DFT calculation.",

keywords = "CO, Chiral epoxides, Cyclic carbonates, Electrosynthesis",

author = "Yan Xiao and Chen, \{Bao Li\} and Yang, \{Heng Pan\} and Huan Wang and Lu, \{Jia Xing\}",

year = "2014",

month = jun,

doi = "10.1016/j.elecom.2014.03.012",

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volume = "43",

pages = "71--74",

journal = "Electrochemistry Communications",

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T1 - Electrosynthesis of enantiomerically pure cyclic carbonates from CO 2 and chiral epoxides

AU - Xiao, Yan

AU - Chen, Bao Li

AU - Yang, Heng Pan

AU - Wang, Huan

AU - Lu, Jia Xing

PY - 2014/6

Y1 - 2014/6

N2 - In this paper, the one-step synthesis of enantiomerically pure cyclic carbonates has been developed by electrolyzing the chiral epoxides and CO 2 (0.1 MPa, rt) in an undivided cell with a 316 stainless steel (SS) cathode and a Mg sacrificial anode containing TEAI-MeCN as supporting electrolyte and solvent with a constant current. To deeply understand this reaction, the effects of various synthesis conditions were investigated using R-styrene oxide as the model compound. Under the optimized conditions, the maximum conversion is 67% with 96% selectivity and 98.8% ee value for R-styrene carbonate. Finally, the reaction mechanism has been proposed by comparative electrolysis and DFT calculation.

AB - In this paper, the one-step synthesis of enantiomerically pure cyclic carbonates has been developed by electrolyzing the chiral epoxides and CO 2 (0.1 MPa, rt) in an undivided cell with a 316 stainless steel (SS) cathode and a Mg sacrificial anode containing TEAI-MeCN as supporting electrolyte and solvent with a constant current. To deeply understand this reaction, the effects of various synthesis conditions were investigated using R-styrene oxide as the model compound. Under the optimized conditions, the maximum conversion is 67% with 96% selectivity and 98.8% ee value for R-styrene carbonate. Finally, the reaction mechanism has been proposed by comparative electrolysis and DFT calculation.

KW - CO

KW - Chiral epoxides

KW - Cyclic carbonates

KW - Electrosynthesis

UR - https://www.scopus.com/pages/publications/84898076108

U2 - 10.1016/j.elecom.2014.03.012

DO - 10.1016/j.elecom.2014.03.012

M3 - 文章

AN - SCOPUS:84898076108

SN - 1388-2481

VL - 43

SP - 71

EP - 74

JO - Electrochemistry Communications

JF - Electrochemistry Communications

ER -

Electrosynthesis of enantiomerically pure cyclic carbonates from CO ₂ and chiral epoxides

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Keywords

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