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A CO2-induced ROCO2Na/ROCO2H buffer solution promoted the carboxylative cyclization of propargyl alcohol to synthesize cyclic carbonates

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Abstract

A CO2-induced ROCO2Na/ROCO2H buffer solution is developed and employed in the carboxylative cyclization of propargyl alcohol to generate α-alkylene cyclic carbonates. The introduction of CO2 into the propargyl alcohol/sodium tertiary pentoxide system can provide the ROCO2Na/ROCO2H buffer solution with both basic and acidic species. The basic and acidic species can simultaneously promote the generation of a carbonate anion intermediate and the interaction between the alkyne moieties of propargyl alcohol and protons (H+), facilitating carboxylative cyclization. Furthermore, the bulky (n-C4H9)4N+ cation of tetrabutylammonium bromide as an additive plays a crucial role in enhancing the nucleophilicity of the carbonate anion intermediate. Various α-alkylene cyclic carbonates are obtained in this catalytic system with relatively good yields at 80 °C.

Graphical abstract: A CO2-induced ROCO2Na/ROCO2H buffer solution promoted the carboxylative cyclization of propargyl alcohol to synthesize cyclic carbonates

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Article information


Submitted
14 Nov 2019
Accepted
12 Dec 2019
First published
12 Dec 2019

Catal. Sci. Technol., 2020, Advance Article
Article type
Paper

A CO2-induced ROCO2Na/ROCO2H buffer solution promoted the carboxylative cyclization of propargyl alcohol to synthesize cyclic carbonates

S. Yan, R. Zhou, F. Han, M. Feng, C. Miao, S. Zhang and S. Ai, Catal. Sci. Technol., 2020, Advance Article , DOI: 10.1039/C9CY02311A

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