Efficient asymmetric hydrogenation of quinolines in neat water catalyzed by chiral cationic Ru-diamine complexes

Yang, Zhusheng; Chen, Fei; He, Yong; Yang, Nuo; Fan, Qing‐Hua

doi:10.1039/c4cy00418c

Cited by 36 publications

(17 citation statements)

References 72 publications

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“…Cationic chiral N –sulfonylated diamine functionalized organometallic complexes, a type of catalytically efficient active species for asymmetric transfer hydrogenation (ATH) reaction, have obvious superiority in catalytic process with respect to their corresponding neutral ones since cationic complexes as real active species based on mechanism study could significantly favor asymmetric transfer hydrogenation process of ketones especially in an aqueous medium (Noyori and Hashiguchi, 1997 ; Liu et al, 2004a , b ; Gladiali and Alberico, 2006 ; Wu et al, 2006 , 2008 ; Ikariya and Blacker, 2007 ; Ohkuma et al, 2007 ; Wang et al, 2008 , 2011 , 2013b ; Ding et al, 2013 ; Yang et al, 2014 , 2016 ; Zhang et al, 2015 ). Therefore, direct immobilization of cationic ruthenium active species within the FDU−12 is beneficial to enhance ATH transformation.…”

Section: Resultsmentioning

confidence: 99%

Boron Tetrafluoride Anion Bonding Dual Active Species Within a Large–Pore Mesoporous Silica for Two–Step Successive Organic Transformaion to Prepare Optically Pure Amino Alcohols

Yang

Zhao

et al. 2018

Front. Chem.

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Development of a simple and easy handing process for preparation of multifunctional heterogenous catalysts and exploration of their applications in sequential organic transformation are of great significance in heterogeneous asymmetric catalysis. Herein, through the utilization of a BF4- anion–bonding strategy, we anchor conveniently both organic bases and chiral ruthenium complex into the nanopores of Me-FDU−12, fabricating a Lewis base/Ru bifunctional heterogeneous catalyst. As we envisaged, cyclic amine as a Lewis base promotes an intermolecular aza–Michael addition between enones and arylamines, affording γ-secondary amino ketones featuring with aryl motif, whereas ruthenium/diamine species as catalytic promoter boosts an asymmetric transfer hydrogenation of γ-secondary amino ketones to γ-secondary amino alcohols. As expected, both enhance synergistically the aza–Michael addition/asymmetric transfer hydrogenation one–pot enantioselective organic transformation, producing chiral γ-secondary amino alcohols with up to 98% enantioselectivity. Unique features, such as operationally simple one–step synthesis of heterogeneous catalyst, homo–like catalytic environment as well as green sustainable process make this heterogeneous catalyst an attracting in a practical preparation of optically pure pharmaceutical intermediates of antidepressants.

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Section: Resultsmentioning

confidence: 99%

Boron Tetrafluoride Anion Bonding Dual Active Species Within a Large–Pore Mesoporous Silica for Two–Step Successive Organic Transformaion to Prepare Optically Pure Amino Alcohols

Yang

Zhao

et al. 2018

Front. Chem.

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“…The most convenient route to chiral tetrahydroquinolines is the asymmetric reduction of quinolines. In continuing our research into ATH, we found that the protocol developed for highly efficient reduction of ketones could also been applied to ATH of cyclic C=N bonds with a slight modification of the tosylated diamine ligand and adjusting the solution pH 39,40…”

Section: Th With Noyori–ikariya‐type Catalysts In Watermentioning

confidence: 99%

Transfer Hydrogenation in Water

Wang

Xiao

2016

The Chemical Record

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This article provides an account of our group's efforts in developing aqueous-phase transfer hydrogenation reactions. It is comprised of mainly two parts. The first part concentrates on asymmetric transfer hydrogenation in water, enabled by Noyori-Ikariya catalysts, while the second part is concerned with the achiral version of the reaction catalysed by a new class of catalysts, iridacycles. A range of substrates are featured, including various carbonyl compounds and N-heterocycles.

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“…Water has been applied as reaction media catalyzed by chiral Ru‐diamine complexes as described in 2014 [61].…”

Section: The Strategies For Hydrogenationmentioning

confidence: 99%

Advances in the reduction of quinolines to 1,2,3,4‐tetrahydroquinolines

El‐Shahat

2021

Journal of Heterocyclic Chem

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The pursuit of modern sustainable chemistry has stimulated the development of innovative catalytic processes that enable chemical transformations to be performed under mild and clean conditions with high efficiency. Herein, we report that the hydrogenation of heteroaromatic compounds is one of the most efficient methods for the construction of heterocyclic skeletons, and only a few promising progress has been achieved. Transition metal‐catalyzed, a countless number of transition metals include have been used toward the development of homo/heterogeneous hydrogenation of quinolines via the most convenient route (Direct Hydrogenation) to obtain the corresponding tetrahydroquinoline derivatives.

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Efficient asymmetric hydrogenation of quinolines in neat water catalyzed by chiral cationic Ru-diamine complexes

Abstract: The first highly effective and enantioselective hydrogenation of quinolines catalyzed by chiral cationic Ru-diamine complexes in undegassed water was developed.

Cited by 36 publications

References 72 publications

Boron Tetrafluoride Anion Bonding Dual Active Species Within a Large–Pore Mesoporous Silica for Two–Step Successive Organic Transformaion to Prepare Optically Pure Amino Alcohols

Boron Tetrafluoride Anion Bonding Dual Active Species Within a Large–Pore Mesoporous Silica for Two–Step Successive Organic Transformaion to Prepare Optically Pure Amino Alcohols

Transfer Hydrogenation in Water

Advances in the reduction of quinolines to 1,2,3,4‐tetrahydroquinolines

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