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Synthesis, characterization and application of Ru(BINAP) (Acac) (MNAA) (MeOH), a highly effective catalyst for the asymmetric hydrogenation of 2-(6′-methoxynaphth-2′-yl)acrylic acid |
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| Authors: | Chih-Chiang Chen Ting-Ti Huang Ching-Wen Lin Rong Cao Albert SC Chan and Wing Tak Wong |
| Institution: | aUnion Laboratory of Asymmetric Synthesis and Department of Applied Biology and Chemical Technology, The Hong Kong Polytechnic University, Humg Hom, Kowloon, Hong Kong, China bDepartment of Chemistry, The University of Hong Kong, Hong Kong, China |
| Abstract: | Ru(S-BINAP) (Acac) (MNAA) (MeOH) (1) (where MNAA (2) = 2-(6′-methoxynaphth-2′-yl)acrylate anion), a highly effective catalyst for the asymmetric hydrogenation of 2-(6′-methoxynaphth-2′-yl) acrylic acid (3), was isolated from a dichloromethane/methanol (vol./vol. = 1/4) solution of Ru(S-BINAP) (Acac)2 and excess of 2-(6′-methoxynaphth-2′-yl)acrylic acid after the solution was exposed to visible light for 2 weeks. On side by side comparison studies, the rate of the hydrogenation of 3 catalyzed by 1 was found to be substantially faster than the same reaction catalyzed by Ru(S-BINAP) (OAc)2. The molecular structure of 1 was unambiguously characterized by single crystal X-ray diffraction. |
| Keywords: | Asymmetric hydrogenation Ruthenium complexes BINAP complexes Acetylacetonate complexes Acrylate anion complexes |
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