Efficient single-component nickel catalysts with tetradentate aminopyridine ligands for cycloaddition reactions of CO2 and epoxides under mild conditions†

Congcong Zhang, Minghui Shi, Ning Yu, Bowen Zhang, Feng Han and Chengxia Miao
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Abstract

A series of single-component nickel catalysts (L1-NiBr2/L2-NiBr2/L3-NiBr2) with tetradentate aminopyridine ligands are presented, which exhibit excellent capabilities and selectivity for the synthesis of cyclic carbonates from epoxides and carbon dioxide. A green crystal of L1-NiBr2 was obtained in CH3CN, and the ligand adopted a cis-α conformation in the complex. The conversion of styrene oxide could reach 98%, providing 100% selectivity at 90 °C, 1 MPa CO2 pressure and 5 mol% of L1-NiBr2 under solvent-free conditions, while the yield and selectivity values were still as high as 92% and 99%, respectively, under 1 atm CO2 and 0.5 mol% of the catalyst at the same temperature. The catalysts also exerted efficient catalytic coupling reactions of terminal epoxides (90–98% yields of cyclic carbonates), except those bearing a long aliphatic chain under mild conditions. The catalyst exhibited excellent recyclability and stability, which were further proved through ICP to test the catalyst leaching, TGA and IR spectra. Moreover, the catalytic cycloaddition reaction mechanism was investigated using density functional theory (DFT) calculations.

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含有四价氨基吡啶配体的高效单组分镍催化剂,可在温和条件下用于 CO2 和环氧化物的环加成反应†。
本文介绍了一系列带有四价氨基吡啶配体的单组分镍催化剂(L1-NiBr2/L2-NiBr2/L3-NiBr2),这些催化剂在以环氧化物和二氧化碳为原料合成环碳酸盐方面表现出卓越的能力和选择性。在 CH3CN 中获得了 L1-NiBr2 的绿色晶体,配体在配合物中呈顺式-α 构象。在无溶剂条件下,当温度为 90 °C、二氧化碳压力为 1 兆帕、L1-NiBr2 的浓度为 5 摩尔时,氧化苯乙烯的转化率可达 98%,选择性为 100%;而在相同温度、二氧化碳压力为 1 兆帕和催化剂浓度为 0.5 摩尔的条件下,产率和选择性仍分别高达 92% 和 99%。在温和条件下,催化剂还能高效催化端环氧化物的偶联反应(环碳酸盐的产率为 90-98%),但带有长脂肪族链的端环氧化物除外。该催化剂具有优异的可回收性和稳定性,这一点通过 ICP 催化剂浸出测试、TGA 和红外光谱得到了进一步证实。此外,还利用密度泛函理论(DFT)计算研究了催化环加成反应机理。
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ESG assessment methodology for emerging technologies: plasma versus conventional technology for ammonia production. Back cover Inside back cover What is better to enhance the solubility of hydrophobic compounds in aqueous solutions: eutectic solvents or ionic liquids?† Utilizing advancements in chemical sciences for decarbonization: a pathway to sustainable emission and energy reduction
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