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Synthesis and effective catalytic performance in cycloaddition reactions with CO2 of boronate esters versus N-heterocyclic carbene (NHC)-stabilized boronate esters
Sustainable Energy & Fuels ( IF 5.6 ) Pub Date : 2020-08-31 , DOI: 10.1039/d0se01189d
Ahmet Kilic 1, 2, 3, 4, 5 , Bayram Sobay 1, 2, 3, 4, 5 , Emine Aytar 1, 2, 3, 4, 5 , Rahime Söylemez 1, 2, 3, 4, 5
Affiliation  

A series of boronate esters (1–3) and N-heterocyclic carbene (NHC)-stabilized boronate esters (4–6) were synthesized and characterized by various spectroscopic techniques, including NMR (1H, 13C, and 11B), FT-IR, UV-Vis, LC-MS/MS spectrometry, melting point, and elemental analysis techniques. The boronate esters (1–3) and N-heterocyclic carbene (NHC)-stabilized boronate esters (4–6) (as Lewis acid) rapidly catalyze the coupling of a variety of epoxides and CO2 to obtain cyclic carbonates in the presence of DMAP (as Lewis base) without the organic solvent. Good to excellent yields of various cyclic carbonates were also achieved under suitable conditions (125 °C, 0.5 h, and 1.6 MPa). After seeing the high catalytic performance of boronate ester catalysts, effects of epoxide, base, temperature, CO2 pressure, reaction time and amount of catalyst and base were investigated for these catalysts. The boronate ester (1) and DMAP showed the best catalytic activity (94.3%) and selectivity (97.5%) for the coupling of CO2 and ECH under suitable conditions (125 °C, 0.5 h, and 1.6 MPa).

中文翻译:

硼酸酯与N杂环卡宾(NHC)稳定的硼酸酯的CO2环加成反应的合成及其在环加成反应中的有效催化性能

合成了一系列硼酸酯(1-3)和N-杂环卡宾(NHC)稳定的硼酸酯(4-6),并通过各种光谱技术进行了表征,包括NMR(1 H,13 C和11 B), FT-IR,UV-Vis,LC-MS / MS光谱,熔点和元素分析技术。硼酸酯(1-3)和N-杂环卡宾(NHC)稳定的硼酸酯(4-6)(路易斯酸)迅速催化多种环氧化物与CO 2的偶联在没有有机溶剂的情况下,在DMAP(作为路易斯碱)存在下获得环状碳酸酯。在合适的条件下(125°C,0.5 h和1.6 MPa),各种环状碳酸酯的收率也达到了良好或优异的水平。在看到硼酸酯催化剂的高催化性能后,研究了环氧化物,碱,温度,CO 2压力,反应时间以及催化剂和碱的量的影响。硼酸酯(1)和DMAP在合适的条件下(125°C,0.5 h和1.6 MPa)对CO 2和ECH偶联显示出最佳的催化活性(94.3%)和选择性(97.5%)。
更新日期:2020-09-24
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