2007 Fiscal Year Final Research Report Summary
Selective Synthesis through Dehydrogenative Silylation with Optically Active Gold(I) Complex
| Project/Area Number |
18550088
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| Research Category |
Grant-in-Aid for Scientific Research (C)
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| Allocation Type | Single-year Grants |
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| Section | 一般 |
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| Research Field |
Synthetic chemistry
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| Research Institution | Hokkaido University |
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Principal Investigator |
ITO Hajime Hokkaido University, Faculty of Science, Associate Professor (90282300)
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| Project Period (FY) |
2006 – 2007
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| Keywords | Organic Chemistry / Gold(I) Complex / Asymmetric Synthesis / Silylation / Environmentally Benign Catalyst |
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| Research Abstract |
Efficient synthesis of optically active compounds is important issue in organic synthesis. In addition, development of new reactions for efficient utilization of resources and reduction of wastes have become very important subject. In this study, the new methods involving kinetic resolution of chiral alcohols through dehydrogenative silylation with optically active gold(I) complexes were examined.
As a preliminary experiment, xantphos-type ligands that have different steric bulk were prepared and the gold(I)-catalyzed dehydrogenative silylation with these ligands was studied. The sterically hindered ligands showed high activities. Next, kinetic resolutions of chiral alcohols were tested by using chiral phosphine ligands. Although the optically active alcohols were obtained, the enantiomeric purities of the resultant products were low.
In order to develop more efficient gold(I) catalysts for kinetic resolution, synthesis and characterization of a gold(I) hydride compound, which is expected to be a key intermediate of catalysis, were investigated. Although gold(I) hydride compounds had never been characterized in solution before, the researcher found that the gold hydride secrecies were generated in the gold(I)-catalyzed dehydrogenative silylation of alcohols. The gold(I) hydride species were characterized by H, P, C, NMR and ESI-Mass.
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[Journal Article] Reversible Mechanochromic Luminescence of[(C_6F_5Au)_2(|-1, 4-diisocyanobenzene)]2008
Author(s)
H. Ito, T. Saito, N. Oshima, N. Kitamura, S. Ishizaka, Y.Hinatsu, M. Wakeshima, M. Kato, K. Tsuge, M. Sawamura
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Journal Title
J. Am. Chem. Soc. 130
Pages: 10044-10045
Description
「研究成果報告書概要(和文)」より
Peer Reviewed
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[Journal Article] Reversible Mechanochromic Luminescence of [(C_6F_5Au)_2(μ-1, 4-diisocyanobenzene)]2008
Author(s)
H. Ito, T. Saito, N. Oshima, N. Kitamura, S. Ishizaka, Y. Hinatsu, M. Wakeshima, M. Kato, K. Tsuge, M. Sawamura
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Journal Title
J. Am. Chem. Sac. 130
Pages: 10044-10045
Description
「研究成果報告書概要(欧文)」より
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