【Labs spotlight】 Urabe and Hata Laboratory
Organic Chemistry - The Area Leading Biosciences
The Department has a variety of laboratories for Life Science and Technology, in which cutting-edge innovative research is being undertaken not only in basic science and engineering but also in the areas of medicine, pharmacy, agriculture, and multidisciplinary sciences.
This "Spotlight" series features a laboratory from the Department and introduces you to the laboratory's research projects and outcomes. This time we focus on Urabe and Hata Laboratory.
Degree |
Professor Hirokazu Urabe : Ph.D. 1985 Tokyo Institute of Technology
Associate Professor Takeshi Hata : PhD 2000, Kyoto University |
Areas of Research |
Professor Hirokazu Urabe : Organic Chemistry, Synthetic Organic Chemistry, Organometallic Chemistry, Pharmaceutical Chemistry, Natural Product Chemistry, Green Chemistry
Associate Professor Takeshi Hata : Synthetic Organic Chemistry, Organometallic Chemistry, Natural Product Chemistry, Green Chemistry, Organic Materials Chemistry
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Keywords |
Professor Hirokazu Urabe : Bioactive Compounds, Catalysis, Chemical Biology, Natural Products, Pharmaceuticals, Synthetic Methodology, Total Synthesis
Associate Professor Takeshi Hata : Bioactive Compounds, Catalysis, π-Conjugated Compounds, Synthetic Methodology
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Website |
Urabe and Hata Laboratory (Japanese) |
Research interest
Hirokazu Urabe
- New Synthetic Reactions
- Synthesis of Naturally Occurring Bioactive Compounds
- Synthesis of Artificial Pharmaceuticals
- Economical or Environmentally Benign Synthetic Methodology
Takeshi Hata
- New Synthetic Reactions
- Economical or Environmentally Benign Synthetic Methodology: C-H Bond Activation, One-pot Synthesis
- Synthesis of Biologically and Electronically Important Compounds
Research findings
Selected publications / Hirokazu Urabe
Original papers
- [1] M. Senoo, A. Furukawa, T. Hata, and H. Urabe, "Rh-catalyzed Intramolecular C-H Bond Activation with Triazoles. Preparation of Stereo-defined Pyrrolidines and Other Related Cyclic Compounds," Chem. Eur. J., 22, 890-895 (2016).
- [2] H. Murase, K. Senda, M. Senoo, T. Hata, and H. Urabe, "Rhodium-catalyzed Intramolecular Hydroarylation of 1-Halo-1-alkynes. Regioselective Synthesis of Semihydrogenated Aromatic Heterocycles," Chem. Eur. J., 20, 317-322 (2014).
- [3] M. Yamagishi, K. Nishigai, A. Ishii, T. Hata, and H. Urabe, "Facile Preparation of Indoles and 1,2-Benzothiazine 1,1-Dioxides via Nucleophilic Addition of Sulfonamides to Bromoacetylenes Followed by Pd-Catalyzed Cyclization," Angew. Chem. Int. Ed., 51, 6471-6474 (2012).
- [4] N. Hirone, H. Sanjiki, R. Tanaka, T. Hata, and H. Urabe, "Acceleration of the Substitution of Silanes with Grignard Reagents by Using either LiCl or YCl3/MeLi," Angew. Chem. Int. Ed., 49, 7762-7764 (2010).
- [5] D. Shikanai, H. Murase, T. Hata, and H. Urabe, "Rh-catalyzed Isomerization and Intramolecular Redox Reaction of Alkynyl Ethers Affording Dihydropyrans and Ketoolefins," J. Am. Chem. Soc., 131, 3166-3167 (2009).
- [6] S. Okada,† K. Arayama,† R. Murayama, T. Ishizuka, K. Hara, N. Hirone, T. Hata, and H. Urabe, "Iron-Catalyst-Switched Selective Conjugate Addition of Grignard Reagents. α,β,γ,δ-Unsaturated Amides as Versatile Templates for Asymmetric Three-Component Coupling Process," Angew. Chem. Int. Ed., 47, 6860-6864 (2008). † Equal contribution
- [7] R. Tanaka, H. Sanjiki, and H. Urabe, "Yttrium-Mediated Conversion of Vinyl Grignard Reagent to a 1,2-Dimetalated Ethane and Its Synthetic Application," J. Am. Chem. Soc., 130, 2904-2905 (2008).
- [8] Y. Fukudome, H. Naito, T. Hata, and H. Urabe, "Copper-Catalyzed 1,2-Double Amination of 1-Halo-1-alkynes. Concise Synthesis of Protected Tetrahydropyrazines and Related Heterocyclic Compounds," J. Am. Chem. Soc., 130, 1820-1821 (2008).
- [9] Y. Nobe, K. Arayama, and H. Urabe, "Air-Assisted Addition of Grignard Reagents to Olefins. A Simple Protocol for Three-Component Coupling Process Yielding Alcohols," J. Am. Chem. Soc., 127, 18006-18007 (2005).
- [10] R. Tanaka, A. Yuza, Y. Watai, D. Suzuki, Y. Takayama, F. Sato, and H. Urabe, "One-Pot Synthesis of Metalated Pyridines from Two Acetylenes, a Nitrile, and a Titanium(II) Alkoxide," J. Am. Chem. Soc., 127, 7774-7780 (2005).
Reviews
- [1] H. Urabe and F. Sato, "Titanocene (Cp2Ti(II)" in Encyclopedia of Reagents for Organic Synthesis, 2nd ed.; L. A. Paquette, D. Crich, P. L. Fuchs, G. A. Molander, Eds., Wiley: Chichester, Vol. 12, pp. 9590-9595 (2009).
- [2] F. Sato, H. Urabe, and S. Okamoto, "Synthesis of Organotitanium Complexes from Alkenes and Alkynes, and Their Synthetic Application," Chem. Rev., 100, 2835-2886 (2000).
Selected publications / Takeshi Hata
- [1] T. Hata, H. Gotoh, T. Yokomizo, and H. Urabe, "Iron-catalyzed 1,6-Selective Addition of Aryl Grignard Reagent to tert-Butyl (Z)-5-Phenyl-3-hexenoate," Org. Synth., 91, 307-321 (2014).
- [2] T. Hata, T. Nakada, O. Y. Taek, N. Hirone, and H. Urabe, "Iron-Catalyzed Regio- and Stereoselective Conjugate Addition of Aryl Grignard Reagents to α,β,γ,δ-Unsaturated Sulfones and Its Synthetic Application," Adv. Synth. Catal., 355, 1736-1740 (2013).
- [3] T. Hata, H. Imade, and H. Urabe, "Four Nucleophilic Additions to Alkenynedioic Acid Derivatives in Tandem; Efficient One-pot Synthesis of Bicyclo[4.2.0]octenols," Org. Lett., 14, 2450-2453 (2012).
- [4] T. Hata, S. Iwata, S. Seto, and H. Urabe, "Iron-Catalyzed Synthesis of Allenes from 2-Alken-4-ynoates and Grignard Reagents" Adv. Synth. Catal. 354, 1885-1889 (2012).
- [5] T. Hata, S. Sujaku, N. Hirone, K. Nakano, J. Imoto, H. Imade, and H. Urabe, "Iron-Mediated and -Catalyzed Metallative Cyclization of Electron Withdrawing Group-substituted Alkynes and Alkenes with Grignard Reagents," Chem.-Eur. J., 17, 14593-14602 (2011).
*Find more about the lab and the latest activities at the lab site (Japanese)
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