Department of Applied Chemistry, Faculty of Engineering. Osaka University The CHATANI Group

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Research

Our research interests are primarily focused on the invention ofnew synthetic methodologies, with a particular emphasis on thedesign and development of novel catalytic system by taking advantage ofunique features of transition metal complexes. Research projects under investigation in our group include:

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  • We have successfully developed catalytic reactions via the cleavage of C-H bonds, a long-sought goal for organic chemists. Based on our discoveries, a lot of related researches have been started all over the world.
  • We have found that normally unreactive C-C, C-F, and C-O bonds can be used for organic synthesis by utilizing transition metal catalysts. These findings will lead to the next generation of synthetic methods.
  • We have developed synthetic methodologies that assemble an array of carbo- and heterocyclic compounds from simple and readily available starting materials in a single step. These reactions will provide conceptually novel strategies for the construction of complex molecular frameworks.
  • New organic transformations via unstable organometallic species have been developed. These catalyses contain fundamentally new elemental reactions on the metal center.

1 Catalysis through thActivation of Unreactive Bonds such as C-H,C-C,C-F, and C-O Bonds

y Silylation of a C-H Bond z
A C-H bond can be transformed into a C-Si bond.
Chem. Lett., (3), 396-397(2002)
y Carbonylation of a C-H Bond z
A Direct Acylation of a C-H Bond
J. Org. Chem., 69(13), 4433-4440(2004)
y Coupling of a C-H Bond with Aldehydes z
Addition a C-H Bond of Imidazoles to Polar Groups
Angew. Chem. Int. Ed., 41(15), 2779-2781(2002)
y Cleavage of Acyl-O Bonds in Esters z
A New Protocol of Generating Acyl-Metal Intermediates and their Use in Catalysis
J. Am. Chem. Soc., 123(20), 4849-4850(2001)
J. Org. Chem., 69(17), 5615-5621(2004)

2 New Synthetic Methodologies through an Efficient Capture of Beactive Intermediates

y Skeltal Reorganization of Enynes z
A New Strategy for the Construction of Complex Molecular Frameworks
J. Am. Chem. Soc., 123(35), 10294-10295(2002)
y Vinylidene Intermediates z
A New Method of the Capture of Metal-Carbene Species
and Its Application to Catalysis
Organometallics., 21(19), 3845-3847(2002)
y Benzyne Intermediates z
A New Catalytic Transformation of Highly Unstable Species
J. Am. Chem. Soc., 123(50), 12686-12687(2001)
y Ketene Intermediate z
Intramolecular Trapping of Unstable Species and Its Application to Catalysis
Angew. Chem. Int. Ed., 42(12), 1397-1399(2003)

3 Catalytic Cycloaddition

y Carbonylative Cycloaddition z
New Strategies for the Cyclic Carbonyl Compounds
from Simple Starting Materials in a Single Step
J. Am. Chem. Soc., 122(51), 12663-12674(2000)
J. Org. Chem., 68(4), 1591-1593(2003)
y Isocyanides z
First Catalytc [4+1] Cycloaddition of Enones and Isocyanides
J. Am. Chem. Soc., 125(26), 7812-7813(2003)
J. Org. Chem. Soc., 127(2), 761-766(2005)

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