Dr. Takuji Kawamoto

【Original Articles】

  1. Redox-neutral Tetrafluoroethylation of Aryl Alkynes with 1,1,2,2-Tetrafluoroethane sulfonic acid leading to α-Tetrafluoroethylated Acetophenones
    Kawamoto, T.; Noguchi, K.; Sasaki, R.; Takata, R.; Matsubara, H.; Kamimura, A. 
    Chem. Eur. J. 2021, accepted.
    https://doi.org/10.1002/chem.202100137
  2. Inverse Hydroboration of Imines with NHC-Boranes Is Promoted by Diphenyl Disulfide and Visible Light.
    Kawamoto, T.; Morioka, T.; Noguchi, K.; Curran, D. P.; Kamimura, A.
    Org. Lett. 202123, 1825–1828.
    https://doi.org/10.1021/acs.orglett.1c00230
  3. Hydrodecyanation of Secondary Alkyl Nitriles and Malononitriles to Alkanes using DiMeImd-BH3.
    Kawamoto, T.; Oritani, K.; Kawabata, A.; Morioka, T.; Matsubara, H.; Kamimura, A.
    J. Org. Chem. 2020, 85, 6137.
    http://dx.doi.org/10.1021/acs.joc.0c00105
  4. Highly Cumulated Radical Cascade Reaction of aza-1,6-Enyenes: Stereoselective Synthesis of exo-Methylene Piperidines.
    Kamimura, A.; Itaya, T.; Yoshinaga, T.; Nozawa, R.; Kawamoto, T.; Sumimoto, M.; Uno, H.
    Eur. J. Org. Chem. 2020, 700.
    http://dx.doi.org/10.1002/ejoc.202000034
  5. 2‐Sulfanylhydroquinone Dimer as a Switchable Fluorescent Dye.
    Kamimura, A.; Sakamoto, S.; Umemoto, H.; Kawamoto, T.; Sumimoto, M.
    Chem. Eur. J. 2019, 25, 14081.
    http://dx.doi.org/10.1002/chem.201903436

    Selected as Cover Feature
    http://dx.doi.org/10.1002/chem.201904089
  6. Kawamoto, T.; Sasaki, R.; Kamimura, A.; Matsubara, H.
    The regioselective trifluoromethylation of 1,3-bis(vinyl triflates) in the absence of external trifluoromethyl sources.
    J. Fluorine Chem. 2019, 221, 66–69.
    http://dx.doi.org/10.1016/j.jfluchem.2019.04.002
  7. Kamimura, A.; Shiramatsu, Y.; Kawamoto, T.
    Depolymerization of polyamide 6 in hydrophilic ionic liquids.
    Green Energy and Environment 2019, in press.
    http://dx.doi.org/10.1016/j.gee.2019.01.002

  8. Kamimura, A.; Yoshinaga, T.; Miyazaki, K.; Kawamoto, T.
    Comparison of homofugality among alkyl groups attached to tin atom.
    Heteroatom Chem. 2018, 2, e21469–7. http://dx.doi.org/10.1002/hc.21469
  9. Hayashi, Y.; Kranidiotis-Hisatomi, N.; Sakamoto, D.; Oritani, K.; Kawamoto, T.; Kamimura, A.
    Asymmetric Michael Reaction of Aldehydes and Dicyanoalkenes Catalyzed by Diphenylprolinol Silyl Ether.
    Eur. J. Org. Chem. 2018, 6843–6847. http://dx.doi.org/10.1002/ejoc.201800831
  10. A Theoretical Study on Radical-Based Aminocarbonylation of Aryl Iodides.
    Kawamoto, T.; Matsubara, H.; Fukuyama, T.; Ryu, I.
    Chem. Lett. 2018, 47, 1169–1171.
    http://dx.doi.org/10.1246/cl.180599

  11. Theoretical Calculations for the 1,4-Hydrogen Shift of 1-Hydroxyallyl Radicals Leading to α-Keto Radicals; Prediction of Facilitation by 1-Amino and 3-Tin Substituents.
    Matsubara, H.; Kawamoto, T.; Fukuyama, T.; Ryu, I.
    Chem. Lett. 2018, 47, 1197–1199.
    http://dx.doi.org/10.1246/cl.180522

  12. Development of a microwave-assisted sustainable conversion of furfural hydrazones to functionalised phthalimides in ionic liquids.
    Karaluka, V.; Murata, K.; Masuda, S.; Shiramatsu, Y.; Kawamoto, T.; Hailes, H. C.; Sheppard, T. D.; Kamimura, A.
    RSC Adv. 2018, 8, 22617–22624.
    http://dx.doi.org/10.1039/C8RA03895C

  13. Solubility-switchable ionic liquids: A control of hydrophilicity and hydrophobicity using a protective group.
    Kamimura, A.; Shiramatsu, Y.; Murata, K.; Kawamoto, T.
    Chem. Lett. 2018, 47, 1079–1081.
    http://dx.doi.org/10.1246/cl.180382

  14.  Deltaarenes; novel macrocyclic molecules that are readily available from 1,4-benzoquinone and benzene dithiols.
    Kamimura, A.; Watanabe, R.; Fukumitsu, T.; Ikeda, K.; Kawamoto, T.; Sumimoto, M.; Mori, S.; Uno, H.
    Tetrahedron 2018, 74, 5303–5308.
    http://dx.doi.org/10.1016/j.tet.2018.04.070
  15. Thiol-Catalyzed Radical Decyanation of Aliphatic Nitriles with Sodium Borohydride
    Kawamoto, T.; Oritani, K.; Curran, D. P.; Kamimura, A.
    Org. Lett. 2018, 20, 2084–2087.
    https://dx.doi.org/10.1021/acs.orglett.8b00626
  16. Tris (trimethylsilyl) silane-Mediated Reductive Decyanation and Cyano Transfer Reactions of Malononitriles
    Kawamoto, T.; Shimaya, Y.; Curran, D. P.; Kamimura, A.
    Chem. Lett. 2018, 47, 573–575.
    https://doi.org/10.1246/cl.171231
  17. N-Heterocyclic Carbene Boryl Iodides Catalyze Insertion Reactions of N-Heterocyclic Carbene Boranes and Diazoesters
    Allen, T.H.; Kawamoto, T.; Gardner, S.; Geib, S.J.; Curran, D.P.
    Org. Lett.
    2017, 19, 3680–3683.
    http://dx.doi.org/10.1021/acs.orglett.7b01777
  18. An efficient and selective conversion of sorbitol in ionic liquids: Use of ion exchange resin as a solid acid catalyst
    Kamimura, A.; Murata, K.; Kawamoto, T.
    Tetrahedron Lett.
    2017, 58, 3616–3618.
    http://dx.doi.org/10.1016/j.tetlet.2017.07.105
  19. Synthesis of α-Trifluoromethylated Ketones from Vinyl Triflates in the Absence of External Trifluoromethyl Sources
    Kawamoto, T.; Sasaki, R.; Kamimura, A.
    Angew. Chem. Int. Ed.
    2017, 56, 1342–1345.
    http://dx.doi.org/10.1002/anie.201608591
    Highlighted in Synfacts, 2017, 13. 0072.
    http://dx.doi.org/10.1055/s-0036-1589791
  20. Asymmetric Synthesis of Bicyclic Nitrocyclopropanes from Primary Nitro Compounds and Stereoselective Formation of Tetrahydro-2H-cyclopenta[b]furans via Ring Expansion/Cyclization Reaction
    Kamimura, A.; Moriyama, T.; Ito, Y.; Kawamoto, T.; Uno, H.
    J. Org. Chem.
    2016, 81, 4664–4681.
    http://dx.doi.org/10.1021/acs.joc.6b00566
  21. 1,3-dimethylimidazoyl-2-ylidene borane
    Gardner, S.; Kawamoto, T.; Curran, D.P.
    Org. Synth.
    2016, 92, 342–355.
    http://dx.doi.org/10.15227/orgsyn.092.0342
  22. A radical cascade reaction of aza-1,6-enyne compounds using allyltributyltin
    Kamimura, A.; Miyazaki, K.; Kawamoto, T.; Uno, H.
    Tetrahedron
    2016, 72, 7722–7726.
    http://dx.doi.org/10.1016/j.tet.2016.04.078
  23. Oxidative synthesis of isoxazoline-N-oxide from optically active nitro alcohols
    Moriyama, T.; Kawamoto, T.; Uno, H.; Kamimura, A.
    Heterocycles
    2016, 92, 1479–1489.
    http://dx.doi.org/10.3987/COM-16-13497
  24. An oxidative cyclopropanation reaction of primary nitro compounds using Fe2O3
    Moriyama, T.; Ito, Y.; Koyama, Y.; Kawamoto, T.; Kamimura, A.
    Tetrahedron Lett.
    2016, 57, 3127–3128.
    http://dx.doi.org/10.1016/j.tetlet.2016.06.013
  25. A regioselective double Stille coupling reaction of bicyclic stannolanes
    Kamimura, A.; Tanaka, T.; So, M.; Itaya, T.; Matsuda, K.; Kawamoto, T.
    Org. Biomol. Chem.
    2016, 14, 8109–8122.
    http://dx.doi.org/10.1039/c6ob01018k
  26. Synthesis of 1,3-Dialkylimidazol-2-ylidene Boranes from 1,3-Dialkylimidazolium Iodides and Sodium Borohydride
    Gardner, S.; Kawamoto, T.; Curran, D.P.
    J. Org. Chem.
    2015, 80, 9794–9797.
    http://dx.doi.org/10.1021/acs.joc.5b01682
  27. Photoinduced Aminocarbonylation of Aryl Iodides
    Kawamoto, T.; Sato, A.; Ryu, I.
    Chem. Eur. J.
    2015, 21, 14764–14767.
    http://dx.doi.org/10.1002/chem.201503164
    Selected as Hot Paper.

  28. Radical Reactions of N -Heterocyclic Carbene Boranes with Organic Nitriles: Cyanation of NHC-Boranes and Reductive Decyanation of Malononitriles
    Kawamoto, T.; Geib, S.J.; Curran, D.P.
    J. Am. Chem. Soc.
    2015, 137, 8617–8622.
    http://dx.doi.org/10.1021/jacs.5b04677
  29. Borohydride-mediated radical addition reactions of organic iodides to electron-deficient alkenes
    Kawamoto, T.; Uehara, S.; Hirao, H.; Fukuyama, T.; Matsubara, H.; Ryu, I.
    J. Org. Chem.
    2014, 79, 3999–4007.
    http://dx.doi.org/10.1021/jo500464q
  30. Cyanoborohydride-promoted radical arylation of benzene
    Kawamoto, T.; Sato, A.; Ryu, I.
    Org. Lett.
    2014, 16, 2111–2113.
    http://dx.doi.org/10.1021/ol500614q
  31. A theoretical study on reduction of acyl radicals with borohydride anions
    Kawamoto, T.; Matsubara, H.; Ryu, I.
    Chem. Lett.
    2014, 43, 1140–1142.
    http://dx.doi.org/10.1246/cl.140370
    Selected as Editor’s Choice

  32. Flow Giese reaction using cyanoborohydride as a radical mediator
    Fukuyama, T.; Kawamoto, T.; Kobayashi, M.; Ryu, I.
    Beilstein J. Org. Chem.
    2013, 9, 1791–1796.
    http://dx.doi.org/10.3762/bjoc.9.208
  33. Efficient hydroxymethylation reactions of iodoarenes using CO and 1,3-dimethylimidazol-2-ylidene borane
    Kawamoto, T.; Okada, T.; Curran, D.P.; Ryu, I.
    Org. Lett.
    2013, 15, 2144–2147.
    http://dx.doi.org/10.1021/ol4006294
  34. Radical addition of alkyl halides to formaldehyde in the presence of cyanoborohydride as a radical mediator. A new protocol for hydroxymethylation reaction
    Kawamoto, T.; Fukuyama, T.; Ryu, I.
    J. Am. Chem. Soc.
    2012, 134, 875–877.
    http://dx.doi.org/10.1021/ja210585n
    Highlighted in Synform, 2012, 5.
    http://dx.doi.org/10.1055/s-0031-1290940

    Highlighted in Nachrichten aus der Chemie, 2012, 60, 210.
    http://dx.doi.org/10.1002/nadc.201290114
  35. Stereocontrolled synthesis of substituted bicyclic ethers through oxy-Favorskii rearrangement: Total synthesis of (±)-communiol e
    Kobayashi, S.; Kinoshita, T.; Kawamoto, T.; Wada, M.; Kuroda, H.; Masuyama, A.; Ryu, I.
    J. Org. Chem.
    2011, 76, 7096–7103.
    http://dx.doi.org/10.1021/jo201064h
    Highlighted in Synfacts, 2011, 11. 1160.
    http://dx.doi.org/10.1055/s-0031-1289273
  36. Thermal retro-aldol reaction using fluorous ether F-626 as a reaction medium
    Fukuyama, T.; Kawamoto, T.; Okamura, T.; Denichoux, A.; Ryu, I.
    Synlett
    2010, 2193–2196.
    http://dx.doi.org/10.1055/s-0030-1258501
  37. Black-light-induced radical/ionic hydroxymethylation of alkyl iodides with atmospheric co in the presence of tetrabutylammonium borohydride
    Kobayashi, S.; Kawamoto, T.; Uehara, S.; Fukuyama, T.; Ryu, I.
    Org. Lett.
    2010, 12, 1548–1551.
    http://dx.doi.org/10.1021/ol1002847

【Reviews, Accounts, etc】

  1. Matsubara, H.; Kawamoto, T.; Fukuyama, T.; Ryu, I.
    Applications of Radical Carbonylation and Amine Addition Chemistry: 1,4-Hydrogen Transfer of 1‑Hydroxylallyl Radicals.
    Acc. Chem. Res. 2018, 51, 2023–2035.
    http://dx.doi.org/10.1021/acs.accounts.8b00278

  2. Radical reactions of borohydrides
    Kawamoto, T.; Ryu, I.
    Org. Biomol. Chem.
    2014, 12, 9733–9742.
    http://dx.doi.org/10.1039/c4ob01784f
    Selected as Inside front cover.

  3. Innovative carbonylation methods
    Kawamoto, T.; Fukuyama, T.; Ryu, I.
    有機合成化学協会誌 2014, 72, 493–505.
    http://dx.doi.org/10.5059/yukigoseikyokaishi.72.493
  4. Free radical-mediated hydroxymethylation using CO and HCHO
    Kawamoto, T.; Ryu, I.
    Chimia
    2012, 66, 372–376.
    http://dx.doi.org/10.2533/chimia.2012.372