Asymmetric hydrogenation of aromatic ketones by new recyclable ionic tagged ferrocene–ruthenium catalyst system

Xu, Di; Zhou, Zhiming; Dai, Li; Tang, Li‐Wei; Zhang, Jun

doi:10.1016/j.bmcl.2015.03.023

Cited by 14 publications

(3 citation statements)

References 51 publications

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“…In 2015, Zhang introduced an innovative recyclable ionic-tagged ferrocene-ruthenium catalyst system for the asymmetric hydrogenation of aromatic ketones ( Scheme 17 ) [ 62 ]. The study revealed that the newly developed ferrocene-oxazoline phosphine ligand ( S , Rp )- 35 , incorporating a quaternary ammonium ion group, exhibited outstanding catalytic performance in the hydrogenation reaction, yielding high product yields (up to 99%) and enantioselectivity (up to 99.7% ee ).…”

Section: Applications Of Siloxane-substituted Oxazoline Ferrocene Lig...mentioning

confidence: 99%

Enhancing the Efficacy of Chiral Ligands and Catalysts: Siloxane-Substituted Oxazoline Ferrocenes as Next-Generation Candidates

Dai,

Zhao,

et al. 2024

Molecules

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Since the discovery of classical chiral oxazoline ferrocene ligands in 1995, they have become pivotal in transition metal-catalyzed asymmetric transformations. Over the past decade, a notable evolution has been observed with the emergence of siloxane-substituted oxazoline ferrocenes, demonstrating significant potential as chiral ligands and catalysts. These compounds have consistently delivered exceptional results in diverse and mechanistically distinct transformations, surpassing the capabilities of classical oxazoline ferrocene ligands. This review meticulously delineates the research progress on siloxane-substituted oxazoline ferrocene compounds. It encompasses the synthesis of crucial precursors and desired products, highlights their achievements in asymmetric catalysis reactions, and delves into the exploration of the derivatization of these compounds, emphasizing the introduction of ionophilic groups and their impact on the recovery of transition metal catalysts. In addition to presenting the current state of knowledge, this review propels future research directions by identifying potential topics for further investigation concerning the siloxane-tagged derivatives. These derivatives are poised to be promising candidates for the next generation of highly efficient ligands and catalysts.

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Section: Applications Of Siloxane-substituted Oxazoline Ferrocene Lig...mentioning

confidence: 99%

Enhancing the Efficacy of Chiral Ligands and Catalysts: Siloxane-Substituted Oxazoline Ferrocenes as Next-Generation Candidates

Dai,

Zhao,

et al. 2024

Molecules

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“…Sulfonated bipyridine palladium complexes were applied in the oxidative carbonylation reaction of amine under a biphasic condition of toluene/H 2 O . An ionic-tagged ferrocene–ruthenium catalyst was developed for the asymmetric hydrogenation of aromatic ketones in the biphasic toluene/H 2 O system . In some processes, supercritical carbon dioxide (scCO 2 ) was employed as a clean phase to replace the traditional organic phase in the biphasic system, such as the In(OTf) 3 catalyst was applied in the scCO 2 /ionic liquid biphasic system to catalyze the Friedel–Crafts acylation reaction .…”

Section: Homogeneous Catalysis and Heterogeneous Separationmentioning

confidence: 99%

“…162 An ionic-tagged ferrocene−ruthenium catalyst was developed for the asymmetric hydrogenation of aromatic ketones in the biphasic toluene/H 2 O system. 163 In some processes, supercritical carbon dioxide (scCO 2 ) was employed as a clean phase to replace the traditional organic phase in the biphasic system, such as the In(OTf) 3 catalyst was applied in the scCO 2 /ionic liquid biphasic system to catalyze the Friedel−Crafts acylation reaction. 164 With the development of organic synthesis, as well as sustainable chemistry, ionic salt tagged complex-catalyst-based biphasic catalysis has wide application prospects in the future.…”

Section: Ionic Salt Tagged Nhc Complex Catalystsmentioning

confidence: 99%

Reusable N-Heterocyclic Carbene Complex Catalysts and Beyond: A Perspective on Recycling Strategies

et al. 2018

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With the continuous development of N-heterocyclic carbene (NHC) chemistry during the past decade, NHC metal complexes have gained wide applications in the research field of organometallic catalysis. The recycling and reuse of NHC metal complexes, which have undergone continuous expansion and diversification, can enhance their catalytic performance, extend their range of application, and afford new routes to green chemistry. Taking NHC metal complex catalysts as the main topic, this review intends to present a comprehensive study of recycling strategies of organometallic catalysts. By an elaborative summarization and classification of recycling strategies, a clear picture of all available of recycling strategies for organometallic catalysts is presented and the advantages and disadvantages of various recycling strategies for specific reactions are discussed in detail. This review is written with the hope of serving as a modest spur to induce other scientists' further contributions in the fields of catalyst recycling and sustainable catalysis.

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Iridium‐Catalyzed Asymmetric Hydrogenation of Halogenated Ketones for the Efficient Construction of Chiral Halohydrins

Yin

et al. 2018

Adv Synth Catal

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Iridium-catalyzed asymmetric hydrogenation of prochiral halogenated ketones was successfully developed to prepare various chiral halohydrins with high reactivities and excellent enantioselectivities under basic reaction condition (up to > 99% conversion, 99% yield, > 99% ee). Moreover, gram-scale experiment was performed well in the presence of just 0.005 mol% (S/C = 20 000) Ir/f-amphox catalyst with 99% yield and > 99% ee.

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Asymmetric hydrogenation of aromatic ketones by new recyclable ionic tagged ferrocene–ruthenium catalyst system

Cited by 14 publications

References 51 publications

Enhancing the Efficacy of Chiral Ligands and Catalysts: Siloxane-Substituted Oxazoline Ferrocenes as Next-Generation Candidates

Enhancing the Efficacy of Chiral Ligands and Catalysts: Siloxane-Substituted Oxazoline Ferrocenes as Next-Generation Candidates

Reusable N-Heterocyclic Carbene Complex Catalysts and Beyond: A Perspective on Recycling Strategies

Iridium‐Catalyzed Asymmetric Hydrogenation of Halogenated Ketones for the Efficient Construction of Chiral Halohydrins

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