High-Throughput and Parallel Screening Methods in Asymmetric Hydrogenation

Jäkel, Christoph; Paciello, Rocco

doi:10.1021/cr040675a

Cited by 223 publications

(94 citation statements)

References 220 publications

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“…[2][3][4][5][6][7] Particular success has been achieved in polyolefins R&D, [8,9] where HT screening has greatly expanded the volume, scope, and quality of data available, while minimizing total materials consumption relative to conventional benchtop techniques. A major asset in screening prospective polymerization catalysts is the ease of compiling qualitative reaction profiles by using infrared thermography to monitor reaction exotherms in the standard 96-well plate format.…”

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confidence: 99%

“…[16][17][18] Quantitative analysis typically relies on conventional gas or highperformance liquid chromatography (GC, HPLC) to assay reaction progress and product speciation. [2,7] The relative merits and the technical challenges of parallel vs. fast sequential analysis have been discussed in detail. [4] Acquisition of real-time kinetic profiles using standard serial instruments is suitable only for relatively slow reactions, because the intervals at which each well can be interrogated must accommodate the time required for analysis.…”

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Time as a Dimension in High‐Throughput Homogeneous Catalysis

et al. 2008

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High-throughput screening offers major opportunities to accelerate the discovery and optimization of homogeneously catalyzed reactions. A general method for acquisition of reaction profiles through a high-throughput quenching (HTQ) approach is described, which gives a more accurate picture of catalyst performance, e.g., total productivity, induction periods, selectivity and lifetime, than the customary analysis at a fixed, arbitrary time.

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Time as a Dimension in High‐Throughput Homogeneous Catalysis

et al. 2008

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“…Despite considerable progress in organometallic chemistry in the last few decades, it is often not possible to rationally design ligands and thus the development of new catalysts, especially in industry, often relies on trial-and-error [9][10][11]. This in turn necessitates the fast synthesis and screening of large families of ligands [11][12][13][14][15][16][17]. Systems based on bidentate phosphorus ligands have been shown to be highly successful in asymmetric transition-metal catalysis [18,19], but efficient combinatorial methodologies to facilitate the synthesis and screening of vast libraries of these type of ligands are still lacking.…”

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Solid-Phase Synthesis and Catalytic Screening of Polystyrene Supported Diphosphines

et al. 2016

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“…2007 年, 范青华等将树枝状的手性双膦配体 GnDenBINAP (41)用于铱催化的喹啉的不对称氢化反应中, 结果发现该树枝状手性双膦配体的铱催化剂能够高效、高对映选择性催化喹啉的氢化 [58] (图 24 [59] . 基于手性单磷配体合成方便, 配位灵活等特点发展的 "混合" 配体催化剂以及通过氢键等次级相互作用 "自组装"为手性双膦配体及其催化剂在不对称催化氢化反应中也得到成功的应用, 并促进了高通量筛选高效、高选择性手性配体及催化剂的快速发展 [60] . 2003 年 , Reetz [61] 、Feringa 和 de Vries [62] 等先后发现在脱氢氨基酸酯等的不对称催化氢化反应中采用不同单磷配体"混合"的手性催化剂, 可以取得比含同种单磷配体的手性催化剂更高的对映选择性.…”

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New Progress and Prospects of Transition Metal-Catalyzed Asymmetric Hydrogenation

Xie¹,

Zhou²

2012

Acta Chim. Sinica

164

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Chiral transition metal complexes-catalyzed asymmetric hydrogenation is one of the most efficient methods for the synthesis of optically active compounds, and has been intensively investigated in the past decades. This review presents a brief overview on the progress in the transition metal-catalyzed asymmetric hydrogenation since the beginning of this new century from three aspects: (1) chiral ligands and catalysts; (2) new catalytic asymmetric hydrogenations; (3) new methods and new strategies in asymmetric hydrogenations. Chiral monodentate phosphorus ligands have been a renaissance from the beginning of new century, and many efficient chiral monophosphoramidites such as MonoPhos, SiPhos, DpenPhos have been developed. The chiral phosphine ligands with a chirality on the phosphorus atom (P-chirality), such as BenzP*, ZhanPhos, and TriFer, have also been explored. Chiral ligands with a spiro skeleton have been a highlight of design and synthesis of chiral ligands. The chiral spiro ligands such as SDP, SiPhos, SIPHOX, and SpinPHOX are very efficient in asymmetric hydrogenations. The iridium complexes of chiral spiro pyridine-aminophosphine ligands SpiroPAP is the most efficient molecular catalysts up to now with a turnover number (ratio of converted substrate to catalyst) over 4500000 in the hydrogenation of acetophenone. A number of breakthroughs have been made in the researches on new catalytic asymmetric hydrogenations. Highly enantioslective hydrogenations of unprotected enamines, heteroaromatic compounds, and N-H imines have been developed. New methods and strategies including self-assembled, dendrimerized, and ferromagnetic nanomaterials-loaded chiral catalysts with recyclability and reusability, the catalysts with "mixed" chiral ligands have also been successfully applied in the catalytic asymmetric hydrogenations. However, the chiral transition metal complexes catalyzed asymmetric hydrogenation still has many challenges and is looking forward to new breakthroughs in the future. In addition to the continuous developments of new chiral ligands and catalysts with high efficiency, high enantioselectivity, and high chemoselectivity, new strategies such as co-operative or relay catalysis are becoming focuses of the asymmetric hydrogenations studies.

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High-Throughput and Parallel Screening Methods in Asymmetric Hydrogenation

Cited by 223 publications

References 220 publications

Time as a Dimension in High‐Throughput Homogeneous Catalysis

Time as a Dimension in High‐Throughput Homogeneous Catalysis

Solid-Phase Synthesis and Catalytic Screening of Polystyrene Supported Diphosphines

New Progress and Prospects of Transition Metal-Catalyzed Asymmetric Hydrogenation

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