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Synlett 2012; 23(9): 1343-1348
DOI: 10.1055/s-0031-1290957
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© Georg Thieme Verlag Stuttgart · New York

Cycloaddition of CO2 to Epoxides Catalyzed by N-Heterocyclic Carbene (NHC)–ZnBr2 System under Mild Conditions

Xiang Liu
a   College of Chemistry and Chemical Engineering, Jiangsu Key Laboratory of Green Synthetic Chemistry for Functional Materials, Xuzhou Normal University, Xuzhou, Jiangsu 221116, P. R. of China, Fax: +86(516)83500349   Email: yhshi@xznu.edu.cn
,
Changsheng Cao*
a   College of Chemistry and Chemical Engineering, Jiangsu Key Laboratory of Green Synthetic Chemistry for Functional Materials, Xuzhou Normal University, Xuzhou, Jiangsu 221116, P. R. of China, Fax: +86(516)83500349   Email: yhshi@xznu.edu.cn
,
Yunfei Li
a   College of Chemistry and Chemical Engineering, Jiangsu Key Laboratory of Green Synthetic Chemistry for Functional Materials, Xuzhou Normal University, Xuzhou, Jiangsu 221116, P. R. of China, Fax: +86(516)83500349   Email: yhshi@xznu.edu.cn
,
Pei Guan
a   College of Chemistry and Chemical Engineering, Jiangsu Key Laboratory of Green Synthetic Chemistry for Functional Materials, Xuzhou Normal University, Xuzhou, Jiangsu 221116, P. R. of China, Fax: +86(516)83500349   Email: yhshi@xznu.edu.cn
,
Longguang Yang
a   College of Chemistry and Chemical Engineering, Jiangsu Key Laboratory of Green Synthetic Chemistry for Functional Materials, Xuzhou Normal University, Xuzhou, Jiangsu 221116, P. R. of China, Fax: +86(516)83500349   Email: yhshi@xznu.edu.cn
,
Yanhui Shi*
a   College of Chemistry and Chemical Engineering, Jiangsu Key Laboratory of Green Synthetic Chemistry for Functional Materials, Xuzhou Normal University, Xuzhou, Jiangsu 221116, P. R. of China, Fax: +86(516)83500349   Email: yhshi@xznu.edu.cn
b   State Key Laboratory of Coordination Chemistry, Nanjing University, Nanjing 210093, P. R. of China
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Publication History

Received: 17 February 2012

Accepted after revision: 12 March 2012

Publication Date:
08 May 2012 (online)

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Abstract

A very simple and convenient method toward coupling of CO2 with epoxides catalyzed by NHC/ZnBr2 has been developed. This catalytic system exhibits excellent activity and selectivity in the cycloaddition reactions of CO2 to terminal epoxides. The reactions can even be carried out under CO2 pressure as low as 0.05 MPa and give carbonates in high yields.

Key words

N-heterocyclic carbenes - NHC–CO2 adducts - carbon dioxide - epoxides - cyclic carbonates

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