A New Class of Tunable Dendritic Diphosphine Ligands: Synthesis and Applications in the Ru-Catalyzed Asymmetric Hydrogenation of Functionalized Ketones

A series of tunable G0–G3 dendritic 2,2′‐bis(diphenylphosphino)‐1,1′‐binaphthyl (BINAP) ligands was prepared by attaching polyaryl ether dendrons onto the four phenyl rings on the P atoms. Their ruthenium complexes were employed in the asymmetric hydrogenation of β‐ketoesters, α‐ketoesters, and α‐ke...

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Published inChemistry : a European journal Vol. 20; no. 32; pp. 9969 - 9978
Main Authors Ma, Baode, Miao, Tingting, Sun, Yihua, He, Yanmei, Liu, Ji, Feng, Yu, Chen, Hui, Fan, Qing-Hua
Format Journal Article
LanguageEnglish
Published Weinheim WILEY-VCH Verlag 04.08.2014
WILEY‐VCH Verlag
Wiley
Wiley Subscription Services, Inc
Subjects
asymmetric catalysis
Asymmetry
Catalysis
Catalysts
Chemistry
Chemistry, Multidisciplinary
dendrimers
Ethers
Hydrogenation
Ligands
Physical Sciences
Ruthenium
Science & Technology
Wedges
ligands
BINAP LIGANDS
dendrimers
UNPRECEDENTED ENHANCEMENT
PHOSPHORAMIDITE LIGANDS
COMPLEXES
asymmetric catalysis
hydrogenation
EFFICIENT CATALYSTS
ruthenium
HIGHLY ENANTIOSELECTIVE HYDROGENATION
RECOVERABLE CATALYSTS
HYDROXY ESTERS
ALPHA-HYDROXY
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Abstract A series of tunable G0–G3 dendritic 2,2′‐bis(diphenylphosphino)‐1,1′‐binaphthyl (BINAP) ligands was prepared by attaching polyaryl ether dendrons onto the four phenyl rings on the P atoms. Their ruthenium complexes were employed in the asymmetric hydrogenation of β‐ketoesters, α‐ketoesters, and α‐ketoamides to reveal the effects of dendron size on the catalytic properties. The second‐ and third‐generation catalysts exhibited excellent enantioselectivities, which are remarkably higher than those obtained from the small molecular catalysts and the first‐generation catalyst. Molecular modeling indicates that the incorporation of bulky dendritic wedges can influence the steric environments around the metal center. In addition, the ruthenium catalyst bearing a second‐generation dendritic ligand could be recycled and reused seven times without any obvious decrease in enantioselectivity. Dendron tuning: A series of tunable dendritic BINAP ligands was prepared by attaching polyaryl ether dendrons onto the four phenyl rings on the P atoms and successfully applied in the Ru‐catalyzed asymmetric hydrogenation of β‐ketoesters, α‐ketoesters, and α‐ketoamides (see figure). The dendritic wedges were found to be able to effectively tune the asymmetric induction of the catalysts and excellent enantioselectivities were observed with the larger dendrimers.
AbstractList A series of tunable G0-G3 dendritic 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (BINAP) ligands was prepared by attaching polyaryl ether dendrons onto the four phenyl rings on the P atoms. Their ruthenium complexes were employed in the asymmetric hydrogenation of β-ketoesters, α-ketoesters, and α-ketoamides to reveal the effects of dendron size on the catalytic properties. The second- and third-generation catalysts exhibited excellent enantioselectivities, which are remarkably higher than those obtained from the small molecular catalysts and the first-generation catalyst. Molecular modeling indicates that the incorporation of bulky dendritic wedges can influence the steric environments around the metal center. In addition, the ruthenium catalyst bearing a second-generation dendritic ligand could be recycled and reused seven times without any obvious decrease in enantioselectivity.A series of tunable G0-G3 dendritic 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (BINAP) ligands was prepared by attaching polyaryl ether dendrons onto the four phenyl rings on the P atoms. Their ruthenium complexes were employed in the asymmetric hydrogenation of β-ketoesters, α-ketoesters, and α-ketoamides to reveal the effects of dendron size on the catalytic properties. The second- and third-generation catalysts exhibited excellent enantioselectivities, which are remarkably higher than those obtained from the small molecular catalysts and the first-generation catalyst. Molecular modeling indicates that the incorporation of bulky dendritic wedges can influence the steric environments around the metal center. In addition, the ruthenium catalyst bearing a second-generation dendritic ligand could be recycled and reused seven times without any obvious decrease in enantioselectivity.
A series of tunable G0-G3 dendritic 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (BINAP) ligands was prepared by attaching polyaryl ether dendrons onto the four phenyl rings on the P atoms. Their ruthenium complexes were employed in the asymmetric hydrogenation of [beta]-ketoesters, [alpha]-ketoesters, and [alpha]-ketoamides to reveal the effects of dendron size on the catalytic properties. The second- and third-generation catalysts exhibited excellent enantioselectivities, which are remarkably higher than those obtained from the small molecular catalysts and the first-generation catalyst. Molecular modeling indicates that the incorporation of bulky dendritic wedges can influence the steric environments around the metal center. In addition, the ruthenium catalyst bearing a second-generation dendritic ligand could be recycled and reused seven times without any obvious decrease in enantioselectivity.
A series of tunable G(0)-G(3) dendritic 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (BINAP) ligands was prepared by attaching polyaryl ether dendrons onto the four phenyl rings on the P atoms. Their ruthenium complexes were employed in the asymmetric hydrogenation of beta-ketoesters, alpha-aketoesters, and alpha-ketoamides to reveal the effects of dendron size on the catalytic properties. The second- and third-generation catalysts exhibited excellent enantioselectivities, which are remarkably higher than those obtained from the small molecular catalysts and the first-generation catalyst. Molecular modeling indicates that the incorporation of bulky dendritic wedges can influence the steric environments around the metal center. In addition, the ruthenium catalyst bearing a second-generation dendritic ligand could be recycled and reused seven times without any obvious decrease in enantioselectivity.
A series of tunable G0–G3 dendritic 2,2′‐bis(diphenylphosphino)‐1,1′‐binaphthyl (BINAP) ligands was prepared by attaching polyaryl ether dendrons onto the four phenyl rings on the P atoms. Their ruthenium complexes were employed in the asymmetric hydrogenation of β‐ketoesters, α‐ketoesters, and α‐ketoamides to reveal the effects of dendron size on the catalytic properties. The second‐ and third‐generation catalysts exhibited excellent enantioselectivities, which are remarkably higher than those obtained from the small molecular catalysts and the first‐generation catalyst. Molecular modeling indicates that the incorporation of bulky dendritic wedges can influence the steric environments around the metal center. In addition, the ruthenium catalyst bearing a second‐generation dendritic ligand could be recycled and reused seven times without any obvious decrease in enantioselectivity. Dendron tuning: A series of tunable dendritic BINAP ligands was prepared by attaching polyaryl ether dendrons onto the four phenyl rings on the P atoms and successfully applied in the Ru‐catalyzed asymmetric hydrogenation of β‐ketoesters, α‐ketoesters, and α‐ketoamides (see figure). The dendritic wedges were found to be able to effectively tune the asymmetric induction of the catalysts and excellent enantioselectivities were observed with the larger dendrimers.
A series of tunable G 0 –G 3 dendritic 2,2′‐bis(diphenylphosphino)‐1,1′‐binaphthyl (BINAP) ligands was prepared by attaching polyaryl ether dendrons onto the four phenyl rings on the P atoms. Their ruthenium complexes were employed in the asymmetric hydrogenation of β‐ketoesters, α‐ketoesters, and α‐ketoamides to reveal the effects of dendron size on the catalytic properties. The second‐ and third‐generation catalysts exhibited excellent enantioselectivities, which are remarkably higher than those obtained from the small molecular catalysts and the first‐generation catalyst. Molecular modeling indicates that the incorporation of bulky dendritic wedges can influence the steric environments around the metal center. In addition, the ruthenium catalyst bearing a second‐generation dendritic ligand could be recycled and reused seven times without any obvious decrease in enantioselectivity.
A series of tunable G sub(0)-G sub(3) dendritic 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (BINAP) ligands was prepared by attaching polyaryl ether dendrons onto the four phenyl rings on the P atoms. Their ruthenium complexes were employed in the asymmetric hydrogenation of beta -ketoesters, alpha -ketoesters, and alpha -ketoamides to reveal the effects of dendron size on the catalytic properties. The second- and third-generation catalysts exhibited excellent enantioselectivities, which are remarkably higher than those obtained from the small molecular catalysts and the first-generation catalyst. Molecular modeling indicates that the incorporation of bulky dendritic wedges can influence the steric environments around the metal center. In addition, the ruthenium catalyst bearing a second-generation dendritic ligand could be recycled and reused seven times without any obvious decrease in enantioselectivity. Dendron tuning: A series of tunable dendritic BINAP ligands was prepared by attaching polyaryl ether dendrons onto the four phenyl rings on the P atoms and successfully applied in the Ru-catalyzed asymmetric hydrogenation of beta -ketoesters, alpha -ketoesters, and alpha -ketoamides (see figure). The dendritic wedges were found to be able to effectively tune the asymmetric induction of the catalysts and excellent enantioselectivities were observed with the larger dendrimers.
A series of tunable G0-G3 dendritic 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (BINAP) ligands was prepared by attaching polyaryl ether dendrons onto the four phenyl rings on the P atoms. Their ruthenium complexes were employed in the asymmetric hydrogenation of β-ketoesters, α-ketoesters, and α-ketoamides to reveal the effects of dendron size on the catalytic properties. The second- and third-generation catalysts exhibited excellent enantioselectivities, which are remarkably higher than those obtained from the small molecular catalysts and the first-generation catalyst. Molecular modeling indicates that the incorporation of bulky dendritic wedges can influence the steric environments around the metal center. In addition, the ruthenium catalyst bearing a second-generation dendritic ligand could be recycled and reused seven times without any obvious decrease in enantioselectivity.
Author He, Yanmei
Liu, Ji
Chen, Hui
Feng, Yu
Fan, Qing-Hua
Sun, Yihua
Miao, Tingting
Ma, Baode
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  surname: He
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  organization: Beijing National Laboratory for Molecular Sciences and CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences (CAS), Beijing 100190 (P.R. China)
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  organization: Beijing National Laboratory for Molecular Sciences and CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences (CAS), Beijing 100190 (P.R. China)
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  givenname: Qing-Hua
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  fullname: Fan, Qing-Hua
  email: fanqh@iccas.ac.cn
  organization: Beijing National Laboratory for Molecular Sciences and CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences (CAS), Beijing 100190 (P.R. China)
BackLink https://www.ncbi.nlm.nih.gov/pubmed/25042448$$D View this record in MEDLINE/PubMed
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Issue 32
Keywords ligands
BINAP LIGANDS
dendrimers
UNPRECEDENTED ENHANCEMENT
PHOSPHORAMIDITE LIGANDS
COMPLEXES
asymmetric catalysis
hydrogenation
EFFICIENT CATALYSTS
ruthenium
HIGHLY ENANTIOSELECTIVE HYDROGENATION
RECOVERABLE CATALYSTS
HYDROXY ESTERS
ALPHA-HYDROXY
Language English
License http://onlinelibrary.wiley.com/termsAndConditions#vor
2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
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Notes National Basic Research Program of China - No. 2010CB833300
National Natural Science Foundation of China - No. 21232008; No. 21290194; No. 21221002
Chinese Academy of Sciences
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Snippet A series of tunable G0–G3 dendritic 2,2′‐bis(diphenylphosphino)‐1,1′‐binaphthyl (BINAP) ligands was prepared by attaching polyaryl ether dendrons onto the four...
A series of tunable G 0 –G 3 dendritic 2,2′‐bis(diphenylphosphino)‐1,1′‐binaphthyl (BINAP) ligands was prepared by attaching polyaryl ether dendrons onto the...
A series of tunable G(0)-G(3) dendritic 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (BINAP) ligands was prepared by attaching polyaryl ether dendrons onto the...
A series of tunable G0-G3 dendritic 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (BINAP) ligands was prepared by attaching polyaryl ether dendrons onto the four...
A series of tunable G sub(0)-G sub(3) dendritic 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (BINAP) ligands was prepared by attaching polyaryl ether dendrons...
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SubjectTerms asymmetric catalysis
Asymmetry
Catalysis
Catalysts
Chemistry
Chemistry, Multidisciplinary
dendrimers
Ethers
Hydrogenation
Ligands
Physical Sciences
Ruthenium
Science & Technology
Wedges
Title A New Class of Tunable Dendritic Diphosphine Ligands: Synthesis and Applications in the Ru-Catalyzed Asymmetric Hydrogenation of Functionalized Ketones
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https://www.proquest.com/docview/1551022939
https://www.proquest.com/docview/1777995528
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