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Preparation and structures of a series of phosphorus‐free Nickel(II) diamine complexes and their applications in hydrogenation of acetophenone
Author(s) -
Chen Zilu,
Zeng Mulan,
Zhang Yuzhen,
Zhang Zhong,
Liang Fupei
Publication year - 2010
Publication title -
applied organometallic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.53
H-Index - 71
eISSN - 1099-0739
pISSN - 0268-2605
DOI - 10.1002/aoc.1656
Subject(s) - acetophenone , chemistry , catalysis , transfer hydrogenation , diamine , noyori asymmetric hydrogenation , medicinal chemistry , nickel , hydrogen , inorganic chemistry , polymer chemistry , organic chemistry , ruthenium
To develop economical and phosphorus‐free catalysts for hydrogenation of ketones, three new complexes, [Ni(1 R ,2 R ‐dpen) 2 (H 2 O)Cl] 2 Cl 2 · 2Et 2 O (1), [Ni(1 R ,2 R ‐dpen)(phen)(CH 3 OH) 2 ]Cl 2 ·2CH 3 OH (2) and [Ni(1,8‐dan) 2 (DMF)Cl] 2 Cl 2 · 3H 2 O (3), and three reported compounds, [Ni(opda)(phen)Cl 2 ]·CH 3 OH (4), [Ni(opda) 2 Cl 2 ] (5) and [Ni(1,2‐dach) 2 ]Cl 2 (6), were prepared and the structures of new compounds were determined by single crystal X‐ray diffraction analysis, in which 1 R ,2 R ‐dpen, phen, 1,8‐dan, opda and 1,2‐dach denote 1 R ,2 R ‐1,2‐diphenylethylenediamine, 1,10‐phenanthroline, 1,8‐diaminonaphthalene, o ‐phenylenediamine and 1,2‐diaminocyclohexane, respectively. The catalytic effects for hydrogenation of acetophenone of these compounds were tested. This revealed very poor or no catalytic effects of these complexes in transfer hydrogenation of acetophenone using isopropanol or HCOOHNEt 3 as hydrogen source. However, they presented much better catalytic effects in ionic hydrogenation of acetophenone using H 2 gas as hydrogen source with a dependence of the catalytic effects on the base used in the hydrogenation reactions. The complexes represent a kind of green hydrogenation catalyst, although the conversion in the hydrogenation reactions is not as high as expected. Copyright © 2010 John Wiley & Sons, Ltd.