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

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A CO2-induced ROCO2Na/ROCO2H buffer solution promoted the carboxylative cyclization of propargyl alcohol to synthesize cyclic carbonates
Catalysis Science & Technology ( IF 4.4 ) Pub Date : 2019/12/12 , DOI: 10.1039/c9cy02311a
Shaorui Yan _{1,

2,

3,

4} , Ruinian Zhou _{1,

2,

3,

4} , Feng Han _{1,

2,

3,

4} , Mengmeng Feng _{1,

2,

3,

4} , Chengxia Miao _{1,

2,

3,

4,

5} , Shuai Zhang _{1,

2,

3,

4} , Shiyun Ai _{1,

2,

3,

4}

Affiliation

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.

中文翻译：

CO2诱导的ROCO2Na / ROCO2H缓冲溶液促进了炔丙醇的羧化环化反应，生成环状碳酸酯

开发了CO ₂诱导的ROCO ₂ Na / ROCO ₂ H缓冲溶液，并将其用于炔丙醇的羧化环化反应中生成α-亚烷基环状碳酸酯。将CO ₂引入炔丙醇/五氧化三钠体系可以为ROCO ₂ Na / ROCO ₂ H缓冲溶液提供碱性和酸性物质。碱性和酸性物质可同时促进碳酸根阴离子中间体的生成以及炔丙醇的炔烃部分与质子（H ⁺）之间的相互作用，从而促进羧基化环化。此外，体积大（n -C ₄ H ₉）四丁基溴化铵的₄ N ⁺阳离子作为添加剂在增强碳酸根阴离子中间体的亲核性中起关键作用。在该催化体系中以80℃的较高产率获得了各种α-亚烷基环状碳酸酯。

更新日期：2020-02-13

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