Optimum bifunctionality in a 2-(2-pyridyl-2-ol)-1,10-phenanthroline based ruthenium complex for transfer hydrogenation of ketones and nitriles: impact of the number of 2-hydroxypyridine fragments

Considerable differences in reactivity and selectivity for 2-hydroxypyridine (2-HP) derived ruthenium complexes in transfer hydrogenation are described. Bifunctional Ru( ii )-(phenpy-OH) [phenpy-OH: 2-(2-pyridyl-2-ol)-1,10-phenanthroline] complex ( 2 ) exhibited excellent catalytic activity in trans...

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Bibliographic Details
Published in:Dalton transactions : an international journal of inorganic chemistry 2016-01, Vol.45 (27), p.11162-11171
Main Authors: Paul, Bhaskar, Chakrabarti, Kaushik, Kundu, Sabuj
Format: Article
Language:English
Subjects:
Bearing
Catalytic activity
Hydrogenation
Ketones
Nitriles
Optimization
Ruthenium
Selectivity
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Summary:Considerable differences in reactivity and selectivity for 2-hydroxypyridine (2-HP) derived ruthenium complexes in transfer hydrogenation are described. Bifunctional Ru( ii )-(phenpy-OH) [phenpy-OH: 2-(2-pyridyl-2-ol)-1,10-phenanthroline] complex ( 2 ) exhibited excellent catalytic activity in transfer hydrogenation (TH) of ketones and nitriles. Notably, in comparison with all the reported 2-hydroxypyridine (2-HP) derived ruthenium complexes in transfer hydrogenation, complex 2 displayed significantly higher activity. Additionally, exploiting the metal-ligand cooperativity in complex 2 , chemoselective TH of ketones was achieved and sterically demanding ketones were readily reduced. An outer-sphere mechanism is proposed for this system as exogenous PPh 3 has no significant effect on the rate of this reaction. This is a rare example of a highly active bifunctional Ru( ii ) catalyst bearing only one 2-HP unit. A rare example of a highly active bifunctional Ru( ii ) catalyst containing only one 2-hydroxypyridine (2-HP) unit is presented which exhibited exceptionally high catalytic activity in transfer hydrogenation of ketones and nitriles.
ISSN:1477-9226
1477-9234
DOI:10.1039/c6dt01961g