Ruthenium‐Catalysed Hydrogenation of Aromatic Ketones using Monodentate Phosphoramidite Ligands

Stegink, Bart; Boxtel, Lonneke van; Lefort, Laurent; Minnaard, Adriaan J.; Feringa, Ben L.; Vries, Johannes G. de

doi:10.1002/adsc.201000425

Cited by 10 publications

(3 citation statements)

References 51 publications

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“…The following programme was used for analysis: 50°C (2 min), 50–110°C (5°C min −1 ), 110°C (5 min), 110–150°C (5°C min −1 ), 150–200°C (10°C min −1 ), 200°C (2 min). Retention times: 8a : 12.9 min; 8b : 6.5 min; 8c : 16.9 min; 8d : 22 min; 8e : 24.5 min; 9a : 16.7 min ( R ), 17.3 min ( S ); 9b : 21.7 min ( S ), 22.1 min ( R ); 9c : 20.4, 21.1 min; 9d : 25.2, 25.5 min; 9e : 28.5, 29.1 min.…”

Section: Methodsmentioning

confidence: 99%

Aqueous phase transfer hydrogenation of aryl ketones catalysed by achiral ruthenium(II) and rhodium(III) complexes and their papain conjugates

Madern¹,

Talbi²,

Salmain³

2012

Applied Organom Chemis

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Several ruthenium and rhodium complexes including 2,2 0 -dipyridylamine ligands substituted at the central N atom by an alkyl chain terminated by a maleimide functional group were tested along with a newly synthesized Rh(III) complex of unsubstituted 2,2 0 -dipyridylamine as catalysts in the transfer hydrogenation of aryl ketones in neat water with formate as hydrogen donor. All of them except one led to the secondary alcohol products with conversion rates depending on the metal complex. Site-specific anchoring of the N-maleimide complexes to the single free cysteine residue of the cysteine endoproteinase papain endowed this protein with transfer hydrogenase properties towards 2,2,2-trifluoroacetophenone. Quantitative conversions were reached with the Rh-based biocatalysts, while modest enantioselectivities were obtained in certain reactional conditions.

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Section: Methodsmentioning

confidence: 99%

Aqueous phase transfer hydrogenation of aryl ketones catalysed by achiral ruthenium(II) and rhodium(III) complexes and their papain conjugates

Madern¹,

Talbi²,

Salmain³

2012

Applied Organom Chemis

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“…Chiral monophosphorus ligands were employed in the Rh-catalyzed asymmetric hydrogenation of conjugate alkenes, − , Ru-catalyzed asymmetric hydrogenation of aromatic ketones, and Ir-catalyzed asymmetric hydrogenation of imines with high activities and good enantioselective control, which were summarized in Scheme .…”

Section: Asymmetric Hydrogenationmentioning

confidence: 99%

Chiral Monophosphorus Ligands for Asymmetric Catalytic Reactions

Tang

2016

ACS Catal.

215

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Chiral monophosphorus ligands are playing an important role for the recent advances in asymmetric catalysis. This review summarizes the latest progress in various asymmetric catalytic reactions with the employment of chiral monophosphorus ligands including asymmetric allylic substitution, asymmetric dearomative arylation, asymmetric Heck reaction, asymmetric cross-coupling, asymmetric C–H bond functionalization, asymmetric coupling of π systems, asymmetric addition, asymmetric hydrogenation, and asymmetric organocatalytic reactions. The new reactivity, selectivity, and reaction mechanism enabled by these chiral monophosphorus ligands are discussed.

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“…11 The ruthenium complex 10 with two monophosphoramidite ligands PipPhos and trans-1,2-diaminocyclohexane shows modest to high enantioselectivity (65-97% ee) in the hydrogenation of ketones. 12 Furthermore, the combination of two achiral bulky triarylphosphine ligands PAr 3 with 1,2-diphenylethylenediamine in the chiral ruthenium catalyst 11 gives up to 97% ee in the hydrogenation of aromatic ketones. 13 These results undoubtedly indicated a new approach for the design of chiral ruthenium catalysts.…”

Section: Short Review Syn Thesismentioning

confidence: 99%

Recent Advances in the Development of Chiral Metal Catalysts for the Asymmetric Hydrogenation of Ketones

2014

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This review describes recent advances in the development of chiral metal catalysts for the asymmetric hydrogenation of ketones to give chiral alcohols, important building blocks for biologically active substances such as pharmaceuticals and natural products. Chiral ruthenium-diphosphine/diamine complexes have received intensive study and many efficient chiral ruthenium catalysts bearing chiral diphosphine and diamine ligands have been developed over the past few decades. In addition, chiral ruthenium, iridium, osmium, iron, copper, and palladium complexes with various chiral ligands have also emerged as highly efficient chiral metal catalysts for the asymmetric hydrogenation of ketones. A wide range of ketones are hydrogenated using these chiral metal catalysts to give chiral alcohols with excellent enantioselectivity with high turnover numbers (TONs) and turnover frequencies (TOFs). 1 Introduction 2 Chiral Ruthenium Catalysts 3 Chiral Iridium Catalysts 4 Other Chiral Metal Catalysts 5 Conclusion and Outlook Key words asymmetric hydrogenation, chiral alcohols, chiral metal catalysts, enantioselectivity, ketones Jian-Hua Xie was born in 1968. He received his Ph.D. in 2003 under the supervision of Professor Qi-Lin Zhou at the Institute of Elemento-Organic Chemistry, Nankai University. He then worked at the same institute and was promoted to associate professor in 2005 and then to full professor in 2010. In 2007, he spent one year as a postdoctoral fellow in Prof. Michael Doyle's group at Maryland University. His research interests focus on asymmetric catalysis and the asymmetric synthesis of natural products and chiral drugs. Deng-Hui Bao was born in Hubei Province, China, in 1988. He received his B.S. degree in chemistry from Wuhan University in 2010. He is now studying at the Institute of Elemento-organic Chemistry under the supervision of Prof. Qi-Lin Zhou at Nankai University. His research interests focus on asymmetric catalysis and the synthesis of biologically active compounds. Qi-Lin Zhou obtained his Ph.D. from the Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences in 1987. After several years of postdoctoral research (with Prof. Klaus Müllen, Prof. Andreas Pfaltz, and Prof. Michael Doyle), he started his independent research at the East China University of Science and Technology, China in 1996. In 1999, he moved to the Institute of Elemento-organic Chemistry, Nankai University as Cheung Kong Scholar. His research interests include organometallics, asymmetric catalysis, and the synthesis of biologically active compounds.

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Ruthenium‐Catalysed Hydrogenation of Aromatic Ketones using Monodentate Phosphoramidite Ligands

Cited by 10 publications

References 51 publications

Aqueous phase transfer hydrogenation of aryl ketones catalysed by achiral ruthenium(II) and rhodium(III) complexes and their papain conjugates

Aqueous phase transfer hydrogenation of aryl ketones catalysed by achiral ruthenium(II) and rhodium(III) complexes and their papain conjugates

Chiral Monophosphorus Ligands for Asymmetric Catalytic Reactions

Recent Advances in the Development of Chiral Metal Catalysts for the Asymmetric Hydrogenation of Ketones

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