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Synthesis of Ruthenium Hydride Complexes Containing beta‐Aminophosphine Ligands Derived from Amino Acids and their use in the H 2 ‐Hydrogenation of Ketones and Imines
Author(s) -
AbdurRashid Kamaluddin,
Guo Rongwei,
Lough Alan J.,
Morris Robert H.,
Song Datong
Publication year - 2005
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.200404274
Subject(s) - chemistry , ruthenium , hydride , beta (programming language) , asymmetric hydrogenation , combinatorial chemistry , noyori asymmetric hydrogenation , amino acid , catalysis , organic chemistry , medicinal chemistry , hydrogen , enantioselective synthesis , biochemistry , computer science , programming language
The new complexes RuHCl(PPh 2 CH 2 CHRNH 2 ) 2 and RuHCl(PPh 2 CH 2 CHRNH 2 )(R‐ binap), R=H (Pgly), R=Me [( R )‐Pala] were prepared by the substitution of the PPh 3 ligands in RuHCl(PPh 3 ) 3 or RuHCl(PPh 3 )[( R )‐binap] with beta‐aminophosphines derived from amino acids. The complex trans ‐RuHCl(Pgly)[( R )‐binap] has been characterized by X‐ray crystallography. The complex trans ‐RuHCl[( S )‐Ppro] 2 where ( S )‐Ppro is derived from proline was also prepared and characterized by X‐ray crystallography. These were used as catalyst precursors in the presence of a base (KOPr‐ i or KOBu‐ t ) for the hydrogenation of various ketones and imines to the respective alcohols and amines with H 2 gas (1–11 atm) at room temperature. Acetophenone was hydrogenated to ( S )‐1‐phenylethanol in low ee (up to 40%) when catalyzed by the enantiomerically pure complexes. These complexes are especially active in the hydrogenation of sterically congested and electronically deactivated ketones and imines and are selective for the hydrogenation of CO bonds over CC bonds.