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분자활성 촉매반응 연구단
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Scorpionate Catalysts for Coupling CO2 and Epoxides to Cyclic Carbonates: A Rational Design Approach for Organocatalysts

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Title
Scorpionate Catalysts for Coupling CO2 and Epoxides to Cyclic Carbonates: A Rational Design Approach for Organocatalysts
Author(s)
Mannkyu Hong; Yoseph Kim; Hyejin Kim; Hee Jin Cho; Mu-Hyun Baik; Youngjo Kim
Publication Date
2018-08
Journal
JOURNAL OF ORGANIC CHEMISTRY, v.83, no.16, pp.9370 - 9380
Publisher
AMER CHEMICAL SOC
Abstract
Novel scorpionate-type organocatalysts capable of effectively coupling carbon dioxide and epoxides under mild conditions to afford cyclic propylene carbonates were developed. On the basis of a combined experimental and computational study, a precise mechanistic proposal was developed and rational optimization strategies were identified. The epoxide ring-opening, which requires an iodide as a nucleophile, was enhanced by utilizing an immonium functionality that can form an ion pair with iodide, making the ring opening process intramolecular. The CO2 activation and cyclic carbonate formation were catalyzed by the concerted action of two hydrogen bonds originating from two phenolic groups placed at the claw positions of the scorpionate scaffold. Electronic tuning of the hydrogen bond donors allowed to identify a new catalyst that can deliver >90% yield for a variety of epoxide substrates within 7 h at room temperature under a CO2 pressure of only 10 bar, and is highly recyclable © 2018 American Chemical Society
URI
https://pr.ibs.re.kr/handle/8788114/5919
ISSN
0022-3263
Appears in Collections:
Center for Catalytic Hydrocarbon Functionalizations(분자활성 촉매반응 연구단) > Journal Papers (저널논문)
Files in This Item:
B_Scorpionate-type _acs.joc.8b00722.pdfDownload

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