Asymmetric hydrogenation of aromatic ketones using an iridium(I) catalyst containing ferrocene-based P–N–N tridentate ligands

Nie, Huifang; Zhou, Gang; Wang, Quanjun; Chen, Weiping; Zhang, Shengyong

doi:10.1016/j.tetasy.2013.10.012

Cited by 45 publications

(46 citation statements)

References 42 publications

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“…In sharp contrast, ligand (S c ,R p )-1f with only one chiral carbon center gave disappointing enantioselectivity (entry 6), similar as the result observed in the Ir-catalyzed asymmetric hydrogenation of simple ketones. 20 Further optimization of the reaction conditions by screening different bases didn't improve the hydrogenation outcome. All of the bases tested such as t-BuOK, tBuONa, KOH, NaOH and K 2 CO 3 showed similar results (entries 6-10).…”

Section: Resultsmentioning

confidence: 99%

Ir-catalyzed asymmetric hydrogenation of β-keto esters with chiral ferrocenyl P,N,N-ligands

et al. 2017

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Section: Resultsmentioning

confidence: 99%

Ir-catalyzed asymmetric hydrogenation of β-keto esters with chiral ferrocenyl P,N,N-ligands

et al. 2017

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“…Chen, Zhang and coworkers developed new ferrocene-based analogues of SpiroPAP 5.9 (see Figure 5.13). 77 Ligands 5.9 were applied to the iridium-catalyzed asymmetric ketone hydrogenation: quantitative yields of alcohols were obtained with good enantioselectivities (for S/C= 2000, ee = 60.8-86.6% for the ligand with Ar = 3,5-(tBu)2C6H3 and X = 6-Me).…”

Section: Pnn Ligandsmentioning

confidence: 99%

Chiral Tridentate-Based Ligands

Bandyopadhyay¹,

Sundararaju²,

Poli³

et al. 2021

Chiral Ligands

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“…在此基础上, Milstein 等 [29] 随后又发现吡啶骨架的三齿 P-N-P 和 P-N-N 型钳形钴催化剂也能有效催化脂肪酸酯的氢化, 但对芳香酸酯和三氟乙酸酯没有催化活性. 在环己基己酸酯的氢化中, P-N-P 型钴催化剂 41a (图 6, 27%收率)的催化活性不如 P-N-N 型钴催化剂 41b (85%收率)和 41c (67%收率), 氮原子上含有氢的 P-N-N 型钴催化剂 41b 给出最高的催化活性(2 mol% 41b, 4 mol%三乙基硼氢化钠, 25 [56] 将他们设计和发展的具有吡啶骨架的 PN 3 -类型的钳形钌催化剂用到酯的氢化中, 并发现钌催化剂 45 [57] [58] 在 Song [45] 2017 年 Clarke 等 [63] 基于二茂铁骨架的手性三齿吡啶胺基膦配体发展了锰催化剂 54 [64]…”

Section: 三齿钳形配体及其催化剂unclassified

Recent Progress in Homogeneous Catalytic Hydrogenation of Esters

Gu¹,

Li²,

Xie³

et al. 2019

Acta Chim. Sinica

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The reduction of esters to alcohols is one of the most important chemical transformations in the production of fine chemicals, such as pharmaceuticals, agricultural chemicals, fragrances, and biofuels. Homogeneous catalytic hydrogenation of esters represents a green, atom-economic, and sustainable alternative to conventional stoichiometric approaches, avoiding the generation of large amount of wastes and the difficulties arose in work-up procedure by using metal hydride reductants. Although challenges still exist, significant progress has been made in catalytic hydrogenation of esters over the last ten years. Numerous transition metal catalysts including noble metal (such as ruthenium, osmium, and iridium) complexes and base metal catalysts (such as iron, cobalt, and manganese) have been developed for the hydrogenation of esters. The ligands of the catalysts have been well studied. A wide range of bidentate ligands including diamines, amino-phosphines, pyridine-amines, N-heterocyclic carbene-amines, and bipyridines, tridentate pincer ligands containing diethylamine and pyridine skeletons, tetradentate ligands containing pyridine and bipyridine skeletons have been applied in the hydrogenation of esters. The efficiency of hydrogenation of esters has been significantly improved, and the highest turnover number (TON) reached 90000 for the hydrogenation of benchmark substrates such as ethyl acetate, ethyl benzoate, and γ-valerolactone. A significant breakthrough has also been made in the catalytic asymmetric hydrogenation of esters to chiral primary alcohols. The asymmetric hydrogenations of ketoesters, racemic δ-hydroxyesters, and racemic α-aryl/alkyl substituted lactones provided efficient methods for the asymmetric synthesis of optically active chiral diols including chiral 1,5-diols and 1,4-diols. The significant progress achieved in recent years in the area of homogeneous catalytic hydrogenation of esters to alcohols is presented in this review. The focus of this review are the development of ligands and catalysts, and the advances in the catalytic asymmetric hydrogenation of esters and lactones.

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Asymmetric hydrogenation of aromatic ketones using an iridium(I) catalyst containing ferrocene-based P–N–N tridentate ligands

Cited by 45 publications

References 42 publications

Ir-catalyzed asymmetric hydrogenation of β-keto esters with chiral ferrocenyl P,N,N-ligands

Ir-catalyzed asymmetric hydrogenation of β-keto esters with chiral ferrocenyl P,N,N-ligands

Chiral Tridentate-Based Ligands

Recent Progress in Homogeneous Catalytic Hydrogenation of Esters

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