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Hanamoto Laboratory
Takeshi HANAMOTO, PhD

Title:
Professor
Affiliation:
Faculty of Science and Enginerring
Address:
Honjyo-machi 1, Saga 840-8502, Japan
mail: hanamoto?cc.saga-u.ac.jp. please change"?" to"@")
Members

｡｡D2Daiki KOMATSU
｡｡M2Akihiro KOGAKouki SAKODA

Research area

Selective introduction of fluorine into original organic compounds has become an important aspect of pharmaceutical and material research due to the unique biological and physical properties of fluorine. Therefore, the development of new methods to prepare a wide range or organofluorine compounds remains a significant task. Our research group has drawn attention for developments in the area of building blocks chemistry of one, two, or three- fluorinated aliphatic molecules. Such new versatile fluorinated building blocks should be easy to handle and ready to prepare and robust. We have continuously been working about the development of new fluorinated building blocks with high performance.

Scheme of research

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Current News

The 3rd Tri-U International Joint Symposium 2019 (Saga, 2019, 10)


19th ESFC (European Symposium on Fluorine Chemistry, Warsaw, Poland, 2019, 8)


Interational Conference on Fluorine Chemistry 2019 (Himeji, 2019, 5)


The 2nd Tri-U International Joint Symposium 2018 (Soochow, China, 2018, 11)


The Tri-U International Joint Symposium 2017 (Daegu, S. Korea, 2017, 11)


18th ESFC (European Symposium on Fluorine Chemistry, Kyiv, Ukraine, 2016, 8)


9th French-Japanese Seminar on Fluorine Chemistry (Nice, France, 2015, 8)


Bordeaux Fluorine Days (Bordeaux, France, 2014)


Participation in 17th ESFC (European Symposium on Fluorine Chemistry, Paris, France, 2013)


Publications

  1. A. Koga, M. Matsuda, R. Tanaka, M. Endo, Y. Yamada, T. Hanamoto, "Highly regio- and stereocontrolled preparation of alpha-(trifluoromethyl)-beta-phenylthio)enamines by the hydroamination of in situ-synthesized 1-(trifluoromethyl)-2-(phenylthio)ethyne", Org. Biomol. Chem, 2023, 21, 8528.
  2. D. Komatsu, K. Yamada, T. Hanamoto, "Iodine-Promoted Synthesis of CF3-substituted Dihydroimidazobenzimidazole and CF3-Dihydroimidazoindole via C-N Bond Formation", Org. Biomol. Chem, 2023, 21, 6732.
  3. T. Hanamoto, "Fluorinated vinyl sulfonium salts and their synthetic utilization", Chem. Rec, 2023, 23, e202200270.
  4. R. Tanaka, K. Sato, M. Shiosaki, T. Hanamoto, "Regio- and stereoselective synthesis of tetrasubstituted (E)-(2-chloro-2-fluoro-1-iodovinyl)dimethylphenylsilane and its desilylative sonogashira coupling", Org. Biomol. Chem, 2022, 20, 9142.
  5. T. Kikumura, K. Kamura, T. Hanamoto, "TBAF-initiated vinylation of aldehydes with trimetyl[(Z)-2-phenylsulfanyl)-1-(trifluoromethyl)vinyl]silane", J. Fluorine Chem, 2022, 255-256, 109959.
  6. G. Ikeda, M. Kawasaki, T. Hanamoto, "Sonogashira cross-coupling of (Z)-2-CF3-vinyl benzyl sulfide and access to 4-CF3-3-iodo-2-substituted thiophenes", J. Fluorine Chem, 2021, 248, 109838.
  7. Y. Fujiwara, K. Sato, Y. Yamada, T. Hanamoto, "Synthesis and reactions of (E)-beta-(bromotetrafluoroethyl)vinyl diphenyl sulfonium triflate", J. Fluorine Chem, 2021, 243, 109737.
  8. K. Sato, Y. Yamada, T. Hanamoto, "Access of cis-4-monofluoromethyl-1,3-oxazolidines via a formal [3+2] cycloaddition triggered by BF3・OEt2", J. Fluorine Chem, 2020, 237, 109599.
  9. Y. Fukuda, T. Kikumura, S. Sakoda, G. Ikeda, Y. Nakamura, M. Dojyo, Y. Yamada, T. Hanamoto, "Stereoselective synthesis of (Z)-2-bromo-2-CF3-vinyl phenyl sulfide and its Sonogashira cross-coupling reaction", Synlett, 2019, 30, 837.
  10. Y. Fujiwara, R. Muta, K. Sato, H. Haramura, Y. Yamada, T. Hanamoto, "A gamma-Fluoro-beta-acetoxypropyl sulfonium salt as an equivalent of alpha (fluoromethyl)vinyl sulfonium salt: reagent for the facile synthesis of monofluoromethylated cyclopropanes or aziridines", Synlett, 2018, 29, 2372.
  11. K. Hirotaki, A. Irie, Y. Nakamura, T. Hanamoto, "Three-component one-pot reactions of 2-trifluoromethyl-N-nosyl-aziridine, primary amines, and vinylsulfonium salts for convenient access to CF3-containing piperazines", Synthesis, 2017, 49, 2488. This paper is also cited in Synfacts, 2017, 10, 577.
  12. K. Hirotaki, K. Yamaguchi, T. Hanamoto, "Base-free synthesis of CF3-containing beta-tryptamine derivatives from N-nosyl-2-CF3-aziridine and indoles", Synlett, 2016, 27, 2846.
  13. T. Ishikawa, M. Yoshiki, T. Tanaka, K. Ogata, Y. Yamada, T. Hanamoto, "Regioselective synthesis of difluoromethylated oxazolidines and 2-Imidazolines", Synthesis, 2016, 48, 1322.
  14. F. Kurosato, T. Ishikawa, Y. Yamada, T. Hanamoto, "Convenient synthesis of N-tosyl-2-(difluoromethyl)aziridine and its application to the preparation of difluoromethyl-beta-tryptamine analogues", Synlett, 2015, 26, 1827.
  15. K. Hirotaki, G. Kawazoe, T. Hanamoto, "Facile synthesis of (E)-beta-(trifluoromethyl)styrenes from halothane (HCFC-123B1)", J. Fluorine Chem., 2015, 171, 169.
  16. T. Ishikawa, N. Kasai, Y. Yamada, T. Hanamoto, "Difluoromethyl vinyl sulfonium salt: a one-pot access to difluoromethyl-containing cyclopropanes", Tetrahedron, 2015, 71, 1254.
  17. M. Yoshiki, R. Ishibashi, Y. Yamada, T. Hanamoto, "TiF4-mediated regioselective cycloaddition of 2-(trifluoromethyl)-N-tosylaziridine to nitriles", Org. Lett., 2014, 16, 5509.
  18. K. Hirotaki, Y. Yamada, T. Hanamoto, "Diethylzinc-promoted synthesis of trifluoromethyl-containing tryptamine analogues from indoles and 2-trifluoromethyl-N-(4-toluenesulfonyl)-aziridine", Asian. J. Org. Chem., 2014, 3, 285 .
  19. K. Hirotaki, Y. Takehiro, R. Kamaishi, Y. Yamada, T. Hanamoto, "Synthesis of mono-fluorinated functionalized cyclopropanes and aziridines using alfa-fluorovinyl diphenyl sulfonium salt", Chem. Commun., 2013, 49, 7965
  20. Y. Takehiro, K. Hirotaki, C. Takeshita, H. Furuno, T. Hanamoto, "Regioselective ring-opening reaction of 2-trifluoromethyl-N-tosylaziridine with some nucleophiles under basic conditions", Tetrahedron, 2013, 69, 7448.
  21. K. Hirotaki and T. Hanamoto, "Synthesis of 2-aryl-3-fluoro-5-silylthiophenes vis a cascade reactive sequence", Org. Lett., 2013, 15, 1226. This paper is also cited in Synfacts, 2013, 9, 606.
  22. Y. Goto, M. Shiosaki, T. Hanamoto, M. Yoshida, H. Sawada, "Synthesis and properties of polyfluoro(silyl)acetylene nanoparticles by reaction of fluoro(silyl)acetylenes with triethylamine", Colloid Polym Sci., 2013, 291, 1211.
  23. N. Kasai, R. Maeda, H. Furuno and T. Hanamoto, "A practical synthesis and applications of (E)-diphenyl-beta-(trifluoromethyl)vinylsufonium triflate", Synthesis, 2012, 44, 3489.
  24. R. Maeda, R. Ishibashi, R. Kamaishi, K. Hirotaki, H. Furuno and T. Hanamoto, "AgSbF6-promoted cycloaddition reaction of 2-trifluoromethyl-N-tosylaziridine with aldehydes", Org. Lett., 2011, 13, 6240.
  25. K. Hirotaki and T. Hanamoto, "Mizoroki-Heck reaction of (1-fluorovinyl)methyldiphenylsilane with aryl iodides", J. Org. Chem., 2011, 76, 8564.
  26. M. Shiosaki, M. Unno and T. Hanamoto, "Property and reactivity of fluoro(silyl)acetylenes and fluoro(stannyl)acetylenes", J. Org. Chem., 2010, 75, 8326.
  27. R. Maeda, K. Ooyama, R. Anno, M. Shiosaki, T. Azema and T. Hanamoto, "Preparation and reactions of (beta-trifluoromethyl)vinyl sulfonium salt", Org. Lett., 2010, 12, 2548.
  28. T. Hanamoto and K. Yamada, "Generation and reactions of trifluoromethylethenyl titanium (II) species", J. Org. Chem., 2009, 74, 7559.
  29. T. Hanamoto, R. Anno, K. Yamada, K. Ryu, R. Maeda, K. Aoi and H. Furuno, "beta-Trifluoromethyl-alfa-functionalized-vinyl sulfides as a potential synthetic intermediate", Tetrahedron., 2009, 65, 2757.
  30. T. Hanamoto, E. Hashimoto, M. Miura, H. Furuno and J. Inanaga, "Reaction of N-methyl-5-tributylstannyl-4-fluoro-1H-pyrazole and its application to N-methyl-chromeno[2,3-d]pyrazol-9-one synthesis", J. Org. Chem., 2008, 73, 4736.
  31. T. Hanamoto, R. Anno, K. Yamada and K. Ryu, "Facile synthesis of alpha-functionalized vinyl sulfides bearing beta-trifluoromethyl group: a highly potential CF3-containing building blocks", Tetrahedron. Lett., 2007, 48, 3727.
  32. T. Hanamoto, T. Suetake, Y. Koga, T. Kawanami, H. Furuno and J. Inanaga, "Synthesis and reactions of 5-tributylstannyl-4-fluoropyrazole", Tetrahedron., 2007, 63, 5062.
  33. T. Hanamoto, Y. Iwamoto, Y. Yamada, and R. Anno, "N-Arylation of 4-fluoro-5-trimethylsilyl-1H-pyrazole", J. Fluorine. Chem, 2007, 128, 1126.
  34. T. Hanamoto, M. Egashira, K. Ishizuka, H. Furuno and J. Inanaga, "Synthesis and reactions of 1-methyl-5-tributylstannyl-4-trifluoromethylpyrazole", Tetrahedron., 2006, 62, 6332.
  35. T. Hanamoto, Y. Koga, T. Kawanami, H.Furuno and J. Inanaga, "Synthesis and crystal structure of 1,2,4-trifluoro-3,5,6-tris(triisopropylsilyl)benzene", Tetrahedron. Lett., 2006, 47, 493.
  36. T. Hanamoto, Y. Koga, E. Kido, T. Kawanami, H.Furuno and J. Inanaga, "Palladium catalyzed cross-coupling reaction of 5-tributyl-4-fluoropyrazole", Chem. Commun., 2005, , 2041.
  37. T. Hanamoto, Y. Hakoshima and M. Egashira, "Tributyl(3,3,3-trifluoro-1-propynyl)stannane as an efficient reagent for the preparation of various trifluoromethylated heterocyclic compounds", Tetrahedron. Lett., 2004, 45, 7573.
  38. T. Hanamoto, Y. Koga, T. Kawanami, H.Furuno and J. Inanaga, "Crystal structure of a Dewar Benzene derivative formed from fluoro(triisopropylsilyl)acetylene", Angew. Chem. Int. Ed., 2004, 43, 3582.
  39. T. Hanamoto and T. Kobayashi, "Cross-coupling reactions of (1-fluorovinyl)methyldiphenylsilane with aryl halides and aryl triflates", J. Org. Chem., 2003, 68, 6354.
  40. T. Hanamoto, N. Morita, and K. Shindo, "Synthesis and reactions of (2,2,2-trifluoroethyl)triphenylphosphonium trifluoromethanesulfonate", Eur. J. Org. Chem., 2003, 4279.
  41. T. Hanamoto, K. Handa, and T. Mido, "Palladium-catalyzed carbonylative coupling of (1-fluorovinyl)tributylstannane with aryl halides and aryl triflates", Bull. Chem. Soc. Jpn., 2002, 75, 2497.
  42. T. Hanamoto, K. Korekoda, K. Nakata, K. Handa, Y. Koga, and M. Kondo, "Synthesis and reactivity of (1-fluorovinyl) phenyl sulfoxide as a dienophile", J. Fluorine Chem., 2002, 118, 99.
  43. T. Hanamoto, K. Nishiyama, H. Tateishi, and M. Kondo, "A new route for the synthesis of mono-fluorinated allyl alcohols using the stereoselective Wittig olefination via reaction of (alpha-fluorovinyl)triphenylphosphonium triflate", Synlett, 2001, 1320.
  44. T. Hanamoto, T. Kobayashi, and M. Kondo, "Fluoride ion-assisted cross-coupling reactions of (alpha-fluorovinyl)diphenylmethylsilane with aryl iodides catalyzed by Pd(0)/Cu(I) systems", Synlett, 2001, 281.
  45. T. Hanamoto, K. Shindo, M. Matsuoka, Y. Kiguchi, and M. Kondo, "Synthesis and reactions of alpha-fluorovinylphosphonium salts", J. Chem. Soc., Perkin Trans 1., 2000, 103.
  46. T. Hanamoto, S. Harada, K. Shindo, and M. Kondo, "Fluoride ion-Initiated -alpha-fluorovinylation of carbonyl compounds with alpha-fluorovinyldiphenylmethylsilane", Chem. Commun., 1999, 2397.
  47. T. Hanamoto, Y. Kiguchi, K. Shindo, M. Matsuoka, and M. Kondo, "Preparation and synthetic applications of alpha-fluorovinylphosphonium salts", Chem. Commun., 1999, 151.

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