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Iron Group Hydrides in Noyori Bifunctional Catalysis
1Department of Chemistry, University of Toronto, 80 Saint George Street, Toronto, Ontario, M5S3H6, Canada.
Chemical Record (New York, N.Y.)
|August 16, 2016
Summary
Researchers developed novel hydride catalysts for efficient hydrogenation and asymmetric transfer hydrogenation of various organic compounds. These catalysts, inspired by Noyori
Area of Science:
- Organometallic Chemistry
- Catalysis
- Asymmetric Synthesis
Background:
- The Morris group focuses on developing efficient catalytic systems for hydrogenation reactions.
- Noyori's metal-ligand bifunctional concepts, particularly the hydride-ruthenium amine-hydrogen (HRuNH) design, provide a foundation for catalyst development.
- Efficient asymmetric hydrogenation and transfer hydrogenation of prochiral substrates remain a significant challenge in organic synthesis.
Purpose of the Study:
- To provide an overview of hydride-containing catalysts developed in the Morris group.
- To highlight their application in the efficient hydrogenation of ketones, imines, nitriles, and esters.
- To showcase their utility in asymmetric hydrogenation and transfer hydrogenation of prochiral ketones and imines.
Main Methods:
- Synthesis of various ruthenium and osmium hydride complexes, including hydridochloro, dihydride, and amide species.
- Utilizing monodentate, bidentate, and tetradentate phosphorus and nitrogen donor ligands.
- Investigating catalytic properties for hydrogenation and asymmetric transfer hydrogenation reactions.
- Employing transition state models to elucidate the mechanism of enantioinduction.
Main Results:
- Demonstrated efficient hydrogenation of simple ketones, imines, nitriles, and esters using prepared hydride catalysts.
- Achieved successful asymmetric hydrogenation and transfer hydrogenation of prochiral ketones and imines.
- Identified an effective iron hydride catalyst for asymmetric transfer hydrogenation.
- Established a link between the hydride-metal-nitrogen-hydrogen (HMNH) structure and the sense of enantioinduction.
Conclusions:
- The developed hydride-containing catalysts are effective for a range of hydrogenation and asymmetric transfer hydrogenation reactions.
- The HRuNH design and related structures are crucial for achieving high efficiency and enantioinduction.
- Further exploration of transition state models can aid in understanding and designing enantioselective catalysts.
Keywords:
asymmetric synthesisestershomogeneous catalysishydrogen transferiminesketonestransition metal hydridesMore Related Videos
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