Indan-f-amphox: An Efficient PNN Ligand for Iridium-Catalyzed Asymmetric Hydrogenation of <i>β</i>-Aryl <i>β</i>-Ketoesters

Guo-xian, GU; Hu, Yang; Liu, Shaodong; Dong, Xiu‐Qin; Zhang, Xumu

doi:10.6023/cjoc201910032

Chin. J. Org. Chem.

2020

DOI: 10.6023/cjoc201910032

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Indan-f-amphox: An Efficient PNN Ligand for Iridium-Catalyzed Asymmetric Hydrogenation of β-Aryl β-Ketoesters

GU Guo-xian¹,

Yang Hu²,

Shaodong Liu³

et al.

Abstract: Indan-f-amphox: 可用于铱催化 β-芳基 β-酮酸酯有非常高的反应活性和立体选择性(对应选择性最高 99%, 转化数高达 10000), 适用于多种 β-芳基 β-酮酸酯.

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Homogeneous Catalytic Hydrogenation of Dimethyl Malonate into 1,3-Propanediol

Fang¹,

Li²,

Jin³

et al. 2022

Chinese Journal of Organic Chemistry

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Ruthenium complexes [(PPh3)(o-PPh2C6H4NH2)RuCl2]2 (1), (o-PPh2C6H4NHR)2RuCl2 (R＝H, 2; Me, 3; Et, 4; CH2Ph, 5) and (o-PPh2C6H4NH2)[(CH2NHR)2]RuCl2 (R＝H, 6; Me, 7; Et, 8; i Pr, 9) were applied to the catalytic hydrogenation of dimethyl malonate into methyl 3-hydroxypropanoate or 1,3-propanediol. Targeting on the objective of the catalytic hydrogenation efficiency, the influence factors on the dimethyl malonate conversion and methyl 3-hydroxypropanoate or 1,3-propanediol selectivity, such as the structure of the ruthenium complex, the type and amount of the catalyst assistant and solvent, were well investigated. The results revealed that complex 8 resulted in the best catalytic results. Meanwhile, complex 8 could also catalyze the hydrogenation of diesters such as diethyl malonate. Keywords ruthenium; o-(diphenylphosphino)aniline; dimethyl malonate; 1,3-propanediol 聚对苯二甲酸丙二醇酯(PTT)是继聚对苯二甲酸乙二醇酯(PET)和聚对苯二甲酸丁二醇酯(PBT)之后开发的新型有机高分子芳香族热塑性聚酯产品. 作为 21 世纪最有前途的新型聚酯材料之一, PTT 具有更加优良的物理化学性能 [1] . 然而, 原料 1,3-丙二醇(1,3-PDO)大规模制备的困难在很大程度上制约了 PTT 产业的进一步发展. 目前, 1,3-PDO 主要通过环氧乙烷羰基化法 [2] 和丙烯醛水合氢化法 [3] 等石化路径制备, 但均受到生产效率以及 1,3-PDO 选择性偏低等问题的限制. 此外, 研究人员也发展了甘油氢解法 [4] 以及微生物发酵法 [5] 等制备

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Homogeneous Catalytic Hydrogenation of Dimethyl Malonate into 1,3-Propanediol

Fang¹,

Li²,

Jin³

et al. 2022

Chinese Journal of Organic Chemistry

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Indan-f-amphox: An Efficient PNN Ligand for Iridium-Catalyzed Asymmetric Hydrogenation of β-Aryl β-Ketoesters

Abstract: Indan-f-amphox: 可用于铱催化 β-芳基 β-酮酸酯有非常高的反应活性和立体选择性(对应选择性最高 99%, 转化数高达 10000), 适用于多种 β-芳基 β-酮酸酯.

Cited by 1 publication

References 12 publications

Homogeneous Catalytic Hydrogenation of Dimethyl Malonate into 1,3-Propanediol

Homogeneous Catalytic Hydrogenation of Dimethyl Malonate into 1,3-Propanediol

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