Publication

Dr. Kazunori Nagao

Original publications

  1. Photoredox-Catalyzed Site-Selective Intermolecular C(sp3)–H Alkylation of Tetrahydrofurfuryl Alcohol Derivatives
    1. Abe, R.; Nagao, K.; Seki, T.; Hata, D.; Sasaki, Y.; Ohmiya, H.
    2. Org. Lett. 2025, 27, accepted.
    3. DOI: 10.1021/acs.orglett.4c04439
  2. Deoxygenative Geminal Silylboration of Amides Using Silylboronates: Synthesis and Use of α-Boryl-α-Silylalkylamines
    1. Watanabe, K.; Nagao, K.; Ohmiya, H.
    2. Angew. Chem. Int. Ed. 2024, 63, e202411990.
    3. DOI: 10.1002/anie.202411990
    4. ChemRxiv. 2024
    5. DOI: 10.26434/chemrxiv-2024-55nn
  3. γ-Amino C(sp3)–H Functionalization of Aliphatic Amines through a Light-Driven Triple Catalysis
    1. Nakagawa, M.; Nagao, K.; Ohmiya, H.
    2. ACS Catal. 2024, 14, 8005–8012.
    3. DOI:10.1021/acscatal.4c0200
  4. A Dual Cobalt and Photoredox Catalysis for Hydrohalogenation of Alkenes
    1. Shibutani, S.; Nagao, K.; Ohmiya, H.
    2. J. Am. Chem. Soc. 2024, 146, 4375–4379.
    3. DOI: 10.1021/jacs.3c10133
  5. Synthesis of Tertiary Alkylphosphonate Oligonucleotides through Light-Driven Radical-Polar Crossover Reactions
    1. Ota, K.; Nagao, K.; Hata, D.; Sugiyama, H.; Segawa, Y.; Tokunoh, R.;  Seki, T.; Miyamoto, N.; Sasaki, Y.; Ohmiya, H.
    2. Nat. Commun. 2023, 14, 6856.
    3. DOI: 10.1038/s41467-023-42639-y
  6. Biomimetic Design of an a-Ketoacylphosphonium-Based Light-Activated Oxygenation Auxiliary
    1. Oya, R.; Ota, K.; Fuki, M.; Kobori, Y.; Higashi, M.; Nagao, K.; Ohmiya, H.
    2. Chem. Sci. 2023, 14, 10488–10493.
    3. DOI: 10.1039/D3SC03572G
  7. A Quadruple Catalysis Enabling Intermolecular Branch-Selective Hydroacylation of Styrenes
    1. Takekawa, Y.; Nakagawa, M.; Nagao, K.; Ohmiya, H.
    2. Chem. Eur. J. 2023, 29, e202301484.
    3. DOI: 10.1002/chem.202301484
  8. Light-Driven Radical-Polar Crossover Catalysis Enabling Decarboxylative Fluorination of Redox Active Esters
    1. Takekawa, Y.; Kodo, T.; Nagao, K.; Kakei, H.; Takeuchi, K.; Sasaki, Y.; Ohmiya, H.
    2. Chem. Lett. 2023, 52, 41–43.
    3. DOI: 10.1246/cl.220472
  9. Light-Driven Radical-Polar Crossover Catalysis for Cross-Coupling with Organosilanes
    1. Matsuo, T.; Nagao, K.; Ohmiya, H.
    2. Tetrahedron Lett. 2022, 112, 154231 (Special Issue on “Recent Advances in Photocatalysis for Selective Organic Synthesis”).
    3. DOI: 10.1016/j.tetlet.2022.154231
  10. Organophotoredox-Catalyzed Semipinacol Rearrangement via Radical-Polar Crossover
    1. Kodo, T.; Nagao, K.; Ohmiya, H.
    2. Nat. Commun. 2022, 13, 2684.
    3. DOI: 10.1038/s41467-022-30395-4
  11. A Triple Photoredox/Cobalt/Bronsted Acid Catalysis Enabling Markovnikov Hydroalkoxylation of Unactivated Alkenes
    1. Nakagawa, M.; Matsuki, Y.; Nagao, K.; Ohmiya, H.
    2. J. Am. Chem. Soc. 2022, 144, 7953–7959.
    3. DOI: 10.1021/jacs.2c00527
  12. Reductive Cross-Coupling between Arylaldehydes and (Hetero)aryl Electrophiles Using Silylboronate Reductant
    1. Watanabe, K.; Takeda, M.; Nagao, K.; Ohmiya, H.
    2. Eur. J. Org. Chem. 2022, e202200005 (Virtual Special Collection on “Silicon Chemistry in Organic Synthesis”).
    3. DOI: 10.1002/ejoc.202200005
  13. Molecular Field Analysis Using Computational-Screening Data in Asymmetric N-Heterocyclic Carbene-Copper Catalysis toward Data-driven in silico Catalyst Optimization
    1. Mukai, M.; Nagao, K.; Yamaguchi, S.; Ohmiya, H.
    2. Bull. Chem. Soc. Jpn. 2022 , 95, 271–277 (Selected Paper).
    3. DOI: 10.1246/bcsj.20210349
  14. Radical Relay Trichloromethylacylation of Alkenes through N-Heterocyclic Carbene Catalysis
    1. Kusakabe, M.; Nagao, K.; Ohmiya, H.
    2. Org. Lett. 2021, 23, 5865–5870.
    3. DOI: 10.1021/acs.orglett.1c02639
  15. Organophotoredox-Catalyzed Decarboxylative N-Alkylation of Sulfonamides
    1. Nakagawa, M.; Nagao, K.; Ikeda, Z.; Reynolds, M.; Ibáñez, I.; Wang, J.; Tokunaga, N.; Sasaki, Y.; Ohmiya, H.
    2. ChemCatChem 2021, 13, Early View (part of a joint Special Collection with EurJIC on “Main Group Catalysis”)
    3. DOI: 10.1002/cctc.202100803
  16. Aryl Radical-Mediated N-Heterocyclic Carbene Catalysis
    1. Matsuki, Y.; Ohnishi, N.; Kakeno, Y.; Takemoto, S.; Ishii, T.; Nagao, K.; Ohmiya, H.
    2. Nat. Commun. 2021, 12, 3848.
    3. DOI: 10.1038/s41467-021-24144-2
  17. Decarboxylative N-Alkylation of Azoles Through Visible-Light-Mediated Organophotoredox Catalysis
    1. Kobayashi, R.; Shibutani, S.; Nagao, K.; Ikeda, Z.; Wang, J.; Ibáñez, I.; Reynolds, M.; Sasaki, Y.; Ohmiya, H.
    2. Org. Lett. 2021, 23, 5415–5419.
    3. DOI: 10.1021/acs.orglett.1c01745
  18. Synthesis of Sterically Hindered α-Hydroxycarbonyls through Radical–Radical Coupling
    1. Ota, K.; Nagao, K.; Ohmiya, H.
    2. Org. Lett. 2021, 23, 4420–4425.
    3. DOI: 10.1021/acs.orglett.1c01358
  19. Radical N-Heterocyclic Carbene Catalysis for β-Ketocarbonyl Synthesis
    1. Ishii, T.; Nagao, K.; Ohmiya, H.
    2. Tetrahedron 2021, 91, 132212 (Special Issue on System-Oriented Development of Organocatalysis).
    3. DOI: 10.1016/j.tet.2021.132212
  20. Fluorescent-oxaboroles: Synthesis and Optical Property by Sugar Recognition
    1. Nakano, M.; Nakamura, R.; Sumida, Y.; Nagao, K.; Furuyama, T.; Inagaki, F.; Ohmiya, H.
    2. Chem. Pharm. Bull. 2021, 44, 526–528 (Featured Article).
    3. DOI: 10.1248/cpb.c21-00179
  21. Catalytic Reductive Cross-Coupling between Aromatic Aldehydes and Arylnitriles
    1. Mitsui, A.; Nagao, K.; Ohmiya, H.
    2. Chem. Eur. J. 2021, 27, 7094–7098.
    3. DOI: 10.1002/chem.202100763
  22. Organophotoredox-Catalyzed Three-Component Coupling of Heteroatom Nucleophiles, Alkenes, and Aliphatic Redox Active Esters
    1. Shibutani, S.; Nagao, K.; Ohmiya, H.
    2. Org. Lett. 2021, 23, 1798-1803.
    3. DOI: 10.1021/acs.orglett.1c00211
  23. Transition-Metal-Free Cross-Coupling Using Tertiary Benzylic Organoboronate
    1. Takeda, M.; Nagao, K.; Ohmiya, H.
    2. Angew. Chem. Int. Ed. 2020, 59, 22460–22464.
    3. DOI: 10.1002/anie.202010251
  24. Static to Inducibly Dynamic Stereocontrol: The Convergent Use of Racemic β-Substituted Ketones
    1. DeHovitz, J. S.; Loh, Y. Y.; Kautzky, J. A.; Nagao, K.; Meichan, A. J.; Yamauchi, M.; Davies, I. W.; MacMillan, D. W. C.; Hyster, T. K.
    2. Science 2020, 369, 1113–1118.
    3. DOI: 10.1126/science.abc9909
  25. Direct Synthesis of Dialkyl Ketones from Aliphatic Aldehydes through Radical N-Heterocyclic Carbene Catalysis
    1. Kakeno, Y.; Kusakabe, M.; Nagao, K.; Ohmiya, H.
    2. ACS Catal. 2020, 10, 8524–8529.
    3. DOI: 10.1021/acscatal.0c02849
  26. Reductive Umpolung for Asymmetric Synthesis of Chiral α-Allenic Alcohols
    1. Kondo, Y.; Nagao, K.; Ohmiya, H.
    2. Chem. Commun. 2020, 56, 7471–7474.
    3. DOI: 10.1039/D0CC02619K
  27. Recent Advances in N-Heterocyclic Carbene-Based Radical Catalysis
    1. Ishii, T.; Nagao, K.; Ohmiya, H.
    2. Chem. Sci. 2020, 11, 5630–5636.
    3. DOI: 10.1039/D0SC01538E
  28. Tertiary Alkylations of Aldehydes, Ketones or Imines Using Benzylic Organoboronates and a Base Catalyst
    1. Sato, Y.; Nakamura, K.; Yabushita, K.; Nagao, K.; Ohmiya, H.
    2. Bull. Chem. Soc. Jpn. 2020 , 93, 1065–1069.
    3. DOI: 10.1246/bcsj.20200122
  29. N-Heterocyclic Carbene-Catalyzed Radical Relay Enabling Synthesis of δ-Ketocarbonyls
    1. Ota, K; Nagao, K.; Ohmiya, H.
    2. Org. Lett. 2020, 22, 3922–3925.
    3. DOI: 10.1021/acs.orglett.0c01199
  30. Aliphatic Oxaboroles Enabling Remarkable Recognition of Diol
    1. Arakawa, N.; Nagao, K.; Murakami, R.; Sumida, Y.; Arakawa, H.; Inagaki, F.; Ohmiya, H.
    2. Bull. Chem. Soc. Jpn. 2020​, 93, 576–580.
    3. DOI: 10.1246/bcsj.20200007
  31. Allylic Cross-Ccoupling Using Aromatic Aaldehydes as α-Alkoxyalkyl Anions
    1. Yuasa, A; Nagao, K.; Ohmiya, H.
    2. Beilstein J. Org. Chem. 2020, 16, 185–189.
    3. DOI: 10.3762/bjoc.16.21
  32. Copper-Catalyzed Enantioselective Reductive Cross-Coupling of Aldehydes and Imines
    1. Mitsui, A.; Nagao, K.; Ohmiya, H.
    2. Org. Lett. 2020, 22, 800–803.
    3. DOI: 10.1021/acs.orglett.9b04144
  33. Organophotoredox-Catalyzed Decarboxylative C(sp3)–O Bond Formation
    1. Shibutani, S.; Kodo, T.; Takeda, M.; Nagao, K.; Tokunaga, N.; Sasaki, Y.; Ohmiya, H.
    2. J. Am. Chem. Soc. 2020, 142, 1211–1216.
    3. DOI: 10.1021/jacs.9b12335
  34. N-Heterocyclic Carbene-Catalyzed Radical Relay Enabling Vicinal Alkylacylation of Alkenes
    1. Ishii, T.; Ota, K.; Nagao, K.; Ohmiya, H.
    2. J. Am. Chem. Soc. 2019, 141, 14073–14077.
    3. DOI: 10.1021/jacs.9b07194
  35. Synergistic N-Heterocyclic Carbene/Palladium Catalyzed Aldehyde Acylation of Allylic Amines
    1. Ohnishi, N.; Yasuda, S.; Nagao, K.; Ohmiya, H.
    2. Asian. J. Org. Chem. 2019, 8, 1133–1135.
    3. DOI: 10.1002/ajoc.201900303
  36. N-Heterocyclic Carbene-Catalyzed Decarboxylative Alkylation of Aldehydes
    1. Ishii, T.; Kakeno, Y.; Nagao, K.; Ohmiya, H.
    2. J. Am. Chem. Soc. 2019, 141, 3854–3858.
    3. DOI: 10.1021/jacs.9b00880
  37. Reductive Coupling between Aromatic Aldehydes and Ketones or Imines by Copper Catalysis
    1. Takeda, M.; Mitsui, A.; Nagao, K.; Ohmiya, H.
    2. J. Am. Chem. Soc. 2019, 141, 3664–3669.
    3. DOI: 10.1021/jacs.8b13309
  38. Asymmetric Catalysis Using Aromatic Aldehydes as Chiral α-Alkoxyalkyl Anions
    1. Yabushita, K.; Yuasa, A.; Nagao, K.; Ohmiya, H.
    2. J. Am. Chem. Soc. 2019, 141, 113–117.
    3. DOI: 10.1021/jacs.8b11495
  39. Dehydrative Allylation between Aldehydes and Allylic Alcohols through Synergistic N-Heterocyclic Carbene/Palladium Catalysis
    1. Haruki, H.; Yasuda, S.; Nagao, K.; Ohmiya, H.
    2. Chem. Eur. J. 2019, 25, 724–727 (Front Cover, Cover Profile).
    3. DOI: 10.1002/chem.201805955
  40. Phosphine-Catalyzed Anti-Hydroboration of Internal Alkynes
    1. Nagao, N.; Yamazaki, A.; Ohmiya, H.; Sawamura, M.
    2. Org. Lett. 2018, 20, 1861–1865.
    3. DOI: 10.1021/acs.orglett.8b00390
  41. Phosphine-Catalyzed Anti-Carboboration of Alkynoates with 9-BBN-Based 1,1-Diborylalkanes: Synthesis and Use of Multi-Substituted γ-Borylallylboranes
    1. Yamazaki, A.; Nagao, K.; Iwai, T.; Ohmiya, H.; Sawamura, M.
    2. Angew. Chem. Int. Ed. 2018, 57, 3196–3199.
    3. DOI: 10.1002/anie.201712351
  42. Photoredox-Catalyzed Deuteration and Tritiation of Pharmaceutical Compounds
    1. Loh, Y.Y*.; Nagao, K*.; Hoover, A. J.; Hesk, D.; Rivera, N. R.; Colletti, S. L.; Davies, I. W.; MacMillan, D. W. C.
    2. * These authors contributed equally to this work.
    3. Science 2017, 358, 1182–1187
    4. DOI: 10.1126/science.aap9674
  43. Phosphine-Catalyzed Vicinal Acylcyanation of Alkynoates.
    1. Murayama, H.; Nagao, K.; Ohmiya, H.; Sawamura, M.
    2. Org. Lett. 2016, 18, 1706-1709.
    3. DOI: 10.1021/acs.orglett.6b00677 
  44. Copper-Catalyzed Semihydrogenation of Internal Alkynes with Molecular Hydrogen.
    1. Wakamatsu, T.; Nagao, K.; Ohmiya, H.; Sawamura, M.
    2. Organometallics 2016, 35, 1354-1357.
    3. DOI: 10.1021/acs.organomet.6b00126 
  45. Copper-Catalyzed Stereoselective Conjugate Addition of Alkylboranes to Alkynoates.
    1. Wakamatsu, T.; Nagao, K.; Ohmiya, H.; Sawamura, M.
    2. Beilstein J. Org. Chem. 2015, 11, 2444-2450.
    3. DOI: 10.3762/bjoc.11.265 
  46. Synthesis of 1,1-Diborylalkenes through a Bronsted-base-catalyzed Reaction between Terminal Alkynes and Bis(pinacolato)diboron.
    1. Morinaga, A.; Nagao, K.; Ohmiya, H.; Sawamura, M.
    2. Angew. Chem. Int. Ed. 2015, 54, 15859-15862.
    3. DOI: 10.1002/anie.201509218 
  47. Copper-Catalyzed Enantioselective Allylic Cross-Coupling with Alkylboranes.
    1. Hojoh, K.; Shido, Y.; Nagao, K.; Mori, S.; Ohmiya, H.; Sawamura, M.
    2. Tetrahedron 2015, 71, 65190-6533.
    3. DOI:10.1016/j.tet.2015.05.048 
  48. Copper-Catalyzed γ-Selective and Stereospecific Allylic Cross-Coupling with Secondary Alkylboranes.
    1. Yasuda, Y.; Nagao, K.; Shido, Y.; Mori, S.; Ohmiya, H.; Sawamura, M.
    2. Chem. Eur. J. 2015, 21, 9666-9670.
    3. DOI: 10.1002/chem.201501055 
  49. Copper(I)-Catalyzed Intramolecular Hydroalkoxylation of Unactivated Alkenes.
    1. Murayama, H.; Nagao, K.; Ohmiya, H.; Sawamura, M.
    2. Org. Lett. 2015, 17, 2039-2041.
    3. DOI: 10.1021/acs.orglet.5b00758 
  50. Anti-Selective Vicinal Silaboration and Diboration of Alkynoates through Phosphine Organocatalysis.
    1. Nagao, K.; Ohmiya, H.; Sawamura, M.
    2. Org. Lett. 2015, 17, 1304-1307.
    3. DOI: 10.1021/acs.orglett.5b00305 
  51. Phosphine-Catalyzed Anti-Carboboration of Alkynoates with Alkyl-, Alkenyl-, and Arylboranes.
    1. Nagao, K.; Ohmiya, H.; Sawamura, M.
    2. J. Am. Chem. Soc. 2014, 136, 10605-10608.
    3. DOI: 10.1021/ja506310v 
  52. Synthesis of Trisubstituted Alkenylstannanes through Copper-Catalyzed Three-Component Coupling with Alkylboranes, Alkynoates, and Tributyltin Methoxide.
    1. Wakamatsu, T.; Nagao, K.; Ohmiya, H.; Sawamura, M.
    2. Angew. Chem. Int. Ed. 2013, 52, 11620-11623.
    3. DOI: 10.1002/anie.201305973 
  53. Reversible 1,3-Anti/Syn Stereochemical Courses in Copper-Catalyzed γ-Selective Allyl-Alkyl Coupling between Chiral Allylic Phosphates and Alkylboranes.
    1. Nagao, K.; Yokobori, U.; Makida, Y.; Ohmiya, H.; Sawamura, M.
    2. J. Am. Chem. Soc. 2012, 134, 8982-8987.
    3. DOI: 10.1021/ja302520h 
  54. Functional Group Tolerable Synthesis of Allylsilanes through Copper-Catalyzed γ-Selective Allyl-Alkyl Coupling between Allylic Phosphates and Alkylboranes.
    1. Nagao, K.; Ohmiya, H.; Sawamura, M.
    2. Synthesis 2012, 44, 1535-1541.
    3. DOI: 10.1055/s-0031-1290818 
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