Labs spotlight #38 - Urabe and Hata Laboratory -

Organic Chemistry - The Area Leading Biosciences

March 23, 2017

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.

Professor Hirokazu Urabe and Associate Professor Takeshi Hata

Life Science and Technology
Professor Hirokazu Urabe and Associate Professor Takeshi Hata

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
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
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).