Enantioselective hydrogenation of aromatic ketones catalyzed by Ru complexes of Goodwin-Lions-type sp2N/sp3N hybrid ligands R-BINAN-R'-Py.
Goodwin-Lions-type sp2N/sp3N hybrid ligands R-BINAN-R'-Py possessing a C2 axis binaphthyl skeleton have been designed and synthesized. Combination of the new non-phosphine ligand with Ru(pi-CH2C(CH3)CH2)2(cod) has been revealed to catalyze the hydrogenation of aromatic ketones with high enantioselectivity of up to 99% ee. The reaction proceeds essentially without the need for any bases, but the reactivity is enhanced by the addition of KOt-C4H9 attaining an S/C ratio of up to 10 000. The success should expand the range of possibilities in designing catalysts not only for hydrogenation but also for many other reactions.
Huang
Hanmin
H
Research Center for Materials Science and the Department of Chemistry, Nagoya University, Chikusa, Nagoya 464-8602, Japan.
Okuno
Tomoko
T
Tsuda
Kazuomi
K
Yoshimura
Masahiro
M
Kitamura
Masato
M
D002384:Catalysis; D006860:Hydrogen Bonding; D006865:Hydrogenation; D007659:Ketones / Q000138:chemical synthesis / Q000737:chemistry*; D008024:Ligands; D015394:Molecular Structure; D009281:Naphthalenes / Q000737:chemistry*; D009942:Organometallic Compounds / Q000737:chemistry*; D012428:Ruthenium / Q000737:chemistry*; D013237:Stereoisomerism
D007659:Ketones; D008024:Ligands; D009281:Naphthalenes; D009942:Organometallic Compounds; D012428:Ruthenium