PEOPLE

石山 竜生

Associate Professor

TEL
+81-11-706-6562
E-mail
ishiyamaeng.hokudai.ac.jp
ROOM
Room 4-10, Frontier Research in Applied Sciences Building

発表論文

  • 63.

    Palladium-catalyzed solid-state borylation of aryl halides using mechanochemistry

    Kubota, K.*; Baba, E.; Seo, T.; Ishiyama, T.; Ito, H.* Beilstein J. Org. Chem. 2022, 18, 855.
    DOI: 10.3762/bjoc.18.86

  • 62.

    General Synthesis of Trialkyl- and Dialkylarylsilylboranes: Versatile Silicon Nucleophiles in Organic Synthesis

    Shishido, R.; Uesugi, M.; Takahashi, Rikuro.; Mita, T.; Ishiyama, T.; Kubota, K.*; Ito, H.* J. Am. Chem. Soc. 2020, 142, 14125–14133.
    DOI: 10.1021/jacs.0c03011

  • 61.

    The Direct Dimesitylborylation of Benzofuran Derivatives via an Iridium-Catalyzed C–H Activation with Silyldimesitylborane

    Shishido, R.; Sasaki, I.; Seki, T.; Ishiyama, T.; Ito, H.* Chem. Eur. J. 2019, 25, 12924–12928.
    DOI: 10.1002/chem.201903776

  • 60.

    Solid-State Suzuki-Miyaura Cross-Coupling Reactions: Olefin-Accelerated C–C Coupling Using Mechanochemistry

    Seo, T.; Ishiyama, T.; Kubota, K.*; Ito, H.* Chem. Sci. 2019, 10, 8202–8210.
    DOI: 10.1039/C9SC02185J

  • 59.

    Iridium(I)-Catalyzed C-H Borylation in Air by Using Mechanochemistry

    Pang, Y.; Ishiyama, T.; Kubota, K.*; Ito, H.* Chem. Eur. J. 2019, 25, 4654–4659.
    DOI: 10.1002/chem.201900685

  • 58.

    Iridium(I)-catalyzed C−H Borylation of α,β-Unsaturated Esters with Bis(pinacolato)diboron

    Sasaki, I.; Taguchi, J.; Doi, H.; Ito, H.*; Ishiyama, T.* Chem. Asian J. 2016, 11, 1400–1405.
    DOI: 10.1002/asia.201600078

     

    TOC

  • 57.

    Regioselective C–H Borylation of Heteroaromatic Aldimines with Iridium Complexes

    Sasaki, I.; Ikeda, T.; Amou, T.; Taguchi, J.; Ito, H.; Ishiyama, T. Synlett 2016, 27, 1582–1586.
    DOI: 10.1055/s-0035-1561578

  • 56.

    Catalyst-Controlled Regiodivergent C-H Borylation of Multifunctionalized Heteroarenes by Using Iridium Complexes

    Sasaki, I.; Taguchi, J.; Hiraki, S.; Ito, H.; Ishiyama, T. Chem. Eur. J. 2015, 21, 25, 9236–9241.
    DOI: 10.1002/chem.201500658

    untitled

  • 55.

    Iridium-catalyzed ortho-C- borylation of aromatic aldimines derived from pentafluoroaniline with bis(pinacolate)diboron

    Sasaki, I.; Amou, T.; Ito, H.; Ishiyama, T. Org. Biomol. Chem. 2014, 12, 2041–2044.
    DOI: 10.1039/C3OB42497A

    GA

  • 54.

    Aromatic C- silylation of arenes with 1-hydrosilatrane catalyzed by an iridium(I)/2,9-dimethylphenanthroline (dmphen) complex

    Ishiyama, T.; Saiki, T.; Kishida, E.; Sasaki, I.; Ito, H.; Miyaura, N. Org. Biomol. Chem. 2013, 11, 8162–8165.
    DOI: 10.1039/C3OB41623B

  • 53.

    Iridium(I)-catalyzed vinylic C-H borylation of 1-cycloalkenecarboxylates with bis(pinacolato)diboron

    Sasaki, I.; Doi, H.; Hashimoto, T.; Kikuchi, T.; Ito, H.; Ishiyama, T. Chem. Commun. 2013, 49, 7546–7548.
    DOI: 10.1039/C3CC44149K

    c3cc44149k-2

  • 52.

    Ortho-C-H Borylation of Benzoate Esters with Bis(pinacolato)diboron Catalyzed by Iridium-phosphine Complexes

    Ishiyama, T.; Isou, H.; Kikuchi, T.; Miyaura, N. Chem. Commun. 2010, 46, 159.
    DOI: 10.1039/b910298a

  • 51.

    Vinylic C-H Borylation of Cyclic Vinyl Ethers with Bis(Pinacolato)diboron Catalyzed by an Iridium(I)-dtbpy Complex

    Kikuchi, T.; Takagi, J.; Isou, H.; Ishiyama, T.; Miyaura, N. Chem. Asian J. 2008, 3, 2082.
    DOI: 10.1002/asia.200800157

  • 50.

    Iridium-catalyzed Vinylic C-H Borylation of Cyclic Vinyl Ethers by Bis(pinacolato)diboron

    Kikuchi, T.; Takagi, J.; Ishiyama, T.; Miyaura, N. Chem. Lett. 2008, 37, 664.
    DOI: 10.1246/cl.2008.664

  • 49.

    Practical Synthesis of Pinacolborane for One-pot Synthesis of Unsymmetrical Biaryls via Aromatic C-H Borylation-cross-coupling Sequence

    Kikuchi, T.; Nobuta, Y.; Umeda, J.; Yamamoto, Y.; Ishiyama, T.; Miyaura, N. Tetrahedron 2008, 64, 4967.
    DOI: 10.1016/j.tet.2008.03.102

  • 48.

    Improvements of Efficiency and Regioselectivity in the Iridium(I)-catalyzed Aromatic C-H Silylation of Arenes with Fluorodisilanes

    Saiki, T.; Nishio, Y.; Ishiyama, T.; Miyaura, N. Organometallics 2006, 25, 6068.
    DOI: 10.1021/om050968+

  • 47.

    Regioselective Aromatic C-H Silylation of Five-membered Heteroarenes with Fluorodisilanes Catalyzed by Iridium(I) Complexes

    Ishiyama, T.; Sato, K.; Nishio, Y.; Saiki, T.; Miyaura, N. Chem. Commun. 2005, 5065.
    DOI: 10.1039/b511171d

  • 46.

    Mechanism of the Mild Functionalization of Arenes by Diboron Reagents Catalyzed by Iridium Complexes. Intermediacy and Chemistry of Bipyridine-ligated Iridium Trisboryl Complexes

    Boller, T. M.; Murphy, J. M.; Hapke, M.; Ishiyama, T.; Miyaura, N.; Hartwig, J. F. J. Am. Chem. Soc. 2005, 127, 14263.
    DOI: 10.1021/ja053433g

  • 45.

    Iridium-catalyzed Direct Borylation of Five-membered Heteroarenes by Bis(pinacolato)diboron: Regioselective, Stoichiometric, and Room Temperature Reactions

    Ishiyama, T.; Takagi, J.; Yonekawa, Y.; Hartwig, J. F.; Miyaura, N. Adv. Synth. Catal. 2003, 345, 1103.
    DOI: 10.1002/adsc.200303058

  • 44.

    Palladium-catalyzed Cross-coupling Reaction of Bis(pinacolato)diboron with Vinyl Triflates β-Substituted by a Carbonyl Group: Efficient Synthesis of β-Boryl-α,β-Unsaturated Carbonyl Compounds and their Synthetic Utility

    Ishiyama, T.; Takagi, J.; Kamon, A.; Miyaura, N. J. Organomet. Chem. 2003, 687, 284.
    DOI: 10.1016/s0022-328x(03)00611-9

  • 43.

    Direct Synthesis of Aryl Halosilanes through Iridium(I)-catalyzed Aromatic C-H Silylation by Disilanes

    Ishiyama, T.; Sato, K.; Nishio, Y.; Miyaura, N. Angew. Chem., Int. Ed. 2003, 42, 5346.
    DOI: 10.1002/anie.200352399

  • 42.

    Room Temperature Borylation of Arenes and Heteroarenes Using Stoichiometric Amounts of Pinacolborane Catalyzed by Iridium Complexes in an inert Solvent

    Ishiyama, T.; Nobuta, Y.; Hartwig, J. F.; Miyaura, N. Chem. Commun. 2003, 2924.
    DOI: 10.1039/b311103b

  • 41.

    Transition Metal-catalyzed Borylation of Alkanes and Arenes via C-H Activation

    Ishiyama, T.; Miyaura, N. J. Organomet. Chem. 2003, 680, 3.
    DOI: 10.1016/s0022-328x(03)00176-1

  • 40.

    Palladium-catalyzed Cross-coupling Reaction of Bis(pinacolato)diboron with 1-Alkenyl Halides or Triflates: Convenient Synthesis of Unsymmetrical 1,3-Dienes via the Borylation-coupling Sequence

    Takagi, J.; Takahashi, K.; Ishiyama, T.; Miyaura, N. J. Am. Chem. Soc. 2002, 124, 8001.
    DOI: 10.1021/ja0202255

  • 39.

    Iridium-catalyzed C-H Coupling Reaction of Heteroaromatic Compounds with Bis(pinacolato)diboron: Regioselective Synthesis of Heteroarylboronates

    Takagi, J.; Sato, K.; Hartwig, J. F.; Ishiyama, T.; Miyaura, N. Tetrahedron Lett. 2002, 43, 5649.
    DOI: 10.1002/chin.200244181

  • 38.

    Synthesis of β-Boryl-α,β-Unsaturated Carbonyl Compounds via Palladium-catalyzed Cross-coupling Reaction of Bis(pinacolato)diboron with Vinyl Triflates

    Takagi, J.; Kamon, A.; Ishiyama, T.; Miyaura, N. Synlett 2002, 1880.
    DOI: 10.1055/s-2002-34869

  • 37.

    Mild Iridium-catalyzed Borylation of Arenes. High Turnover Numbers, Room Temperature Reactions, and Isolation of a Potential intermediate

    Ishiyama, T.; Takagi, J.; Ishida, K.; Miyaura, N.; Anastasi, N. R.; Hartwig, J. F. J. Am. Chem. Soc. 2002, 124, 390.
    DOI: 10.1021/ja0173019

  • 36.

    A Stoichiometric Aromatic C-H Borylation Catalyzed by Iridium(I)/2,2′-Bipyridine Complexes at Room Temperature

    Ishiyama, T.; Takagi, J.; Hartwig, J. F.; Miyaura, N. Angew. Chem., Int. Ed. 2002, 41, 3056.
    DOI: 10.1002/chin.200251174

  • 35.

    Nucleophilic Borylation of Benzyl Halides with Bis(pinacolato)diboron Catalyzed by Palladium(0) Complexes

    Ishiyama, T.; Oohashi, Z.; Ahiko, T.; Miyaura, N. Chem. Lett. 2002, 780.
    DOI: 10.1002/chin.200251176

  • 34.

    Acceleration Effect of Lewis Acid in Allylboration of Aldehydes: Catalytic, Regiospecific, Diastereospecific, and Enantioselective Synthesis of Homoallyl Alcohols

    Ishiyama, T.; Ahiko, T.; Miyaura, N. J. Am. Chem. Soc. 2002, 124, 12414.
    DOI: 10.1021/ja0210345

  • 33.

    A Borylcopper Species Generated from Bis(pinacolato)diboron and Its Additions to α,β -Unsaturated Carbonyl Compounds and Terminal Alkynes

    Takahashi, K.; Ishiyama, T.; Miyaura, N. J. Organomet. Chem. 2001, 625, 47.

  • 32.

    Palladium-catalyzed Benzylic C-H Borylation of Alkylbenzenes with Bis(pinacolato)diboron or Pinacolborane

    Ishiyama, T.; Ishida, K.; Takagi, J.; Miyaura, N. Chem. Lett. 2001, 1082.
    DOI: 10.1002/chin.200212196

  • 31.

    Synthesis of Pinacol Arylboronates via Cross-coupling Reaction of Bis(pinacolato)diboron with Chloroarenes Catalyzed by Palladium(0)-Tricyclohexylphosphine Complexes

    Ishiyama, T.; Ishida, K.; Miyaura, N. Tetrahedron 2001, 57, 9813.
    DOI: 10.1016/S0040-4020(01)00998-X

  • 30.

    Synthesis of 1-Alkenylboronic Esters via Palladium-catalyzed Cross-coupling Reaction of Bis(pinacolato)diboron with 1-Alkenyl Halides and Triflates

    Takahashi, K.; Takagi, J.; Ishiyama, T.; Miyaura, N. Chem. Lett. 2000, 126.
    DOI: 10.1002/chin.200024166

  • 29.

    Addition and Coupling Reactions of Bis(pinacolato)diboron Mediated by CuCl in the Presence of Potassium Acetate

    Takahashi, K.; Ishiyama, T.; Miyaura, N. Chem. Lett. 2000, 982.
    DOI: 10.1246/cl.2000.982

  • 28.

    Chemistry of Group 13 Element-Transition Metal Linkage - the Platinum- and Palladium-catalyzed Reactions of (Alkoxo)diborons

    Ishiyama, T.; Miyaura, N. J. Organomet. Chem. 2000, 611, 392.
    DOI: 10.1016/S0022-328X(00)00470-8

  • 27.

    Platinum(0)-catalyzed Diboration of Methylenecyclopropanes with Bis(pinacolato)diboron: a Selective Route to 2,4-Bis(boryl)-1-Butenes

    Ishiyama, T.; Momota, S.; Miyaura, N. Synlett 1999, 1790.
    DOI: 10.1002/chin.200009167

  • 26.

    Synthesis of Organoboron Compounds via the Transition Metal-catalyzed Addition and Coupling Reaction of (Alkoxo)diborons

    Ishiyama, T.; Miyaura, H. J. Synth. Org. Chem. 1999, 57, 503.
    DOI: 10.1002/chin.200114291

  • 25.

    Palladium-catalyzed Carbonylative Cross-coupling Reaction of Arylboronic Acids with Aryl Electrophiles: Synthesis of Biaryl Ketones

    Ishiyama, T.; Kizaki, H.; Hayashi, T.; Suzuki, A.; Miyaura, N. J. Org. Chem. 1998, 63, 4726.
    DOI: 10.1021/jo980417b

  • 24.

    Platinum(0)-catalyzed Diboration of Allenes with Bis(pinacolato)diboron

    Ishiyama, T.; Kitano, T.; Miyaura, N. Tetrahedron Lett. 1998, 39, 2357.
    DOI: 10.1016/S0040-4039(98)00199-3

  • 23.

    Diboration of Alkenes with Bis(pinacolato)diboron Catalysed by a Platinum(0) Complex

    Ishiyama, T.; Yamamoto, M.; Miyaura, N. Chem. Commun. 1997, 689.
    DOI: 10.1002/chin.199733223

  • 22.

    Synthesis of Arylboronates via the Palladium(0)-catalyzed Cross-coupling Reaction of Tetra(alkoxo)diborons with Aryl Triflates

    Ishiyama, T.; Itoh, Y.; Kitano, T.; Miyaura, N. Tetrahedron Lett. 1997, 38, 3447.
    DOI: 10.1016/S0040-4039(97)00642-4

  • 21.

    A Sequence of Palladium-catalyzed Borylation of Allyl Acetates with Bis(pinacolato)diboron and intramolecular Allylboration For the Cyclization of Oxo-2-Alkenyl Acetates

    Ahiko, T. A.; Ishiyama, T.; Miyaura, N. Chem. Lett. 1997, 811.
    DOI: 10.1002/chin.199750056

  • 20.

    Platinum(0)-Catalysed Diboration of Alka-1,3-Dienes with Bis(pinacolato)diboron

    Ishiyama, T.; Yamamoto, M.; Miyaura, N. Chem. Commun. 1996, 2073.
    DOI: 10.1002/chin.199701221

  • 19.

    A Synthesis of (E)-(1-Organo-1-Alkenyl)Boronates by the Palladium-catalyzed Cross-coupling Reaction of (E)-1,2-Bis(boryl)-1-alkenes with Organic Halides: A Formal Carboboration of Alkynes via the Diboration-coupling Sequence

    Ishiyama, T.; Yamamoto, M.; Miyaura, N. Chem. Lett. 1996, 1117.
    DOI: 10.1002/chin.199721173

  • 18.

    the Palladium-catalyzed Cross-coupling Reaction of 9-Organothio-9-Borabicyclo[3.3.1]nonanes with organic Electrophiles: Synthesis of Unsymmetrical Sulfides

    Ishiyama, T.; Mori, M.; Suzuki, A.; Miyaura, N. J. Organomet. Chem. 1996, 525, 225.
    DOI: 10.1002/chin.199718119

  • 17.

    Platinum(0)-catalyzed Diboration of Alkynes with Tetrakis(alkoxo)diborons: An Efficient and Convenient Approach to cis-Bis(boryl) Alkenes

    Ishiyama, T.; Matsuda, N.; Murata, M.; Ozawa, F.; Suzuki, A.; Miyaura, N. Organometallics 1996, 15, 713.
    DOI: 10.1002/chin.199619198

  • 16.

    a Synthesis of Allylboronates via the Palladium(0)-catalyzed Cross-coupling Reaction of Bis(pinacolato)diboron with Allylic Acetates

    Ishiyama, T.; Ahiko, T.; Miyaura, N. Tetrahedron Lett. 1996, 37, 6889.
    DOI: 10.1016/0040-4039(96)01505-5

  • 15.

    Synthesis of Ketones From Iodoalkenes, Carbon-Monoxide and 9-Alkyl-9-Borabicyclo[3,3,1]nonane Derivatives via a Radical Cyclization and Palladium-catalyzed Carbonylative Cross-coupling Sequence

    Ishiyama, T.; Murata, M.; Suzuki, A.; Miyaura, N. Chem. Commun. 1995, 295.
    DOI: 10.1002/chin.199527073

  • 14.

    Palladium(0)-catalyzed Cross-coupling Reaction of Alkoxydiboron with Haloarenes - A Direct Procedure For Arylboronic Esters

    Ishiyama, T.; Murata, M.; Miyaura, N. J. Org. Chem. 1995, 60, 7508.
    DOI: 10.1021/jo00128a024

  • 13.

    Palladium(0)-catalyzed Thioboration of Terminal Alkynes with 9-(Alkylthio)-9-Borabicyclo [3.3.1]nonane Derivatives - Stereoselective Synthesis of Vinyl Sulfides via the Thioboration Cross-coupling Sequence

    Ishiyama, T.; Nishijima, K.; Miyaura, N.; Suzuki, A. J. Am. Chem. Soc. 1993, 115, 7219.
    DOI: 10.1002/chin.199350124

  • 12.

    Platinum(0)-catalyzed Diboration of Alkynes

    Ishiyama, T.; Matsuda, N.; Miyaura, N.; Suzuki, A. J. Am. Chem. Soc. 1993, 115, 11018.
    DOI: 10.1021/ja00076a081

  • 11.

    Synthesis of Unsymmetrical Biaryl Ketones via Palladium-catalyzed Carbonylative Cross-coupling Reaction of Arylboronic Acids with Iodoarenes

    Ishiyama, T.; Kizaki, H.; Miyaura, N.; Suzuki, A. Tetrahedron Lett. 1993, 34, 7595.
    DOI: 10.1016/S0040-4039(00)60409-4

  • 10.

    Palladium-catalyzed Iminocarbonylative Cross-coupling Reaction Between Haloarenes, T-bunc, and 9-Alkyl-9-Bbn Derivatives - Synthesis of Alkyl Aryl Ketones

    Ishiyama, T.; Ohe, T.; Miyaura, N.; Suzuki, A. Tetrahedron Lett. 1992, 33, 4465.
    DOI: 10.1016/S0040-4039(00)60111-9

  • 9.

    Palladium-catalyzed Alkyl-Alkyl Cross-coupling Reaction of 9-Alkyl-9-BBN Derivatives with Iodoalkanes Possessing β-Hydrogens

    Ishiyama, T.; Abe, S.; Miyaura, N.; Suzuki, A. Chem. Lett. 1992, 691.
    DOI: 10.1246/cl.1992.691

  • 8.

    Palladium-catalyzed Carbonylative Cross-coupling Reaction of Iodoalkanes with 9-Alkyl-9-BBN Derivatives - a Direct and Selective Synthesis of Ketones

    Ishiyama, T.; Miyaura, N.; Suzuki, A. Tetrahedron Lett. 1991, 32, 6923.
    DOI: 10.1016/0040-4039(91)80445-C

  • 7.

    Palladium-catalyzed Carbonylative Cross-coupling Reaction of 1-Halo-1-Alkenes with 9-Alkyl-9-BBN Derivatives - A Direct Synthesis of α,β-Unsaturated Ketones

    Ishiyama, T.; Miyaura, N.; Suzuki, A. Bull. Chem. Soc. Jpn. 1991, 64, 1999.
    DOI: 10.1002/chin.199136128

  • 6.

    Synthesis of Functionalized organotin Compounds via Palladium-catalyzed Cross-coupling Reaction of Aryl or 1-Alkenyl Halides with 9-(ω-Stannylalkyl)-9-Borabicyclo[3.3.1]nonanes

    Ishiyama, T.; Miyaura, N.; Suzuki, A. Synlett 1991, 687.
    DOI: 10.1002/chin.199217231

  • 5.

    Palladium-catalyzed intermolecular and intramolecular Cross-coupling Reactions of B-Alkyl-9-Borabicyclo[3.3.1]nonane Derivatives with 1-Halo-1-Alkenes or Haloarenes - Syntheses of Functionalized Alkenes, Arenes, and Cycloalkenes via a Hydroboration Coupling Sequence

    Miyaura, N.; Ishiyama, T.; Sasaki, H.; Ishikawa, M.; Satoh, M.; Suzuki, A. J. Am. Chem. Soc. 1989, 111, 314.
    DOI: 10.1021/ja00183a048

  • 4.

    A Stereoselective Route to Alkenyl Sulfides Through the Palladium-catalyzed Cross-coupling Reaction of 9-Alkyl-9-BBN with 1-Bromo-1-Phenylthioethene or (E)-2-Bromo-1-Phenylthio-1-Alkenes and (Z)-2-Bromo-1-Phenylthio-1-Alkenes

    Hoshino, Y.; Ishiyama, T.; Miyaura, N.; Suzuki, A. Tetrahedron Lett. 1988, 29, 3983.

  • 3.

    Stereoselective Synthesis of Conjugated Dienones via the Palladium-catalyzed Cross-coupling Reaction of 1-Alkenylboronates with 3-Halo-2-Alken-1-Ones

    Satoh, N.; Ishiyama, T.; Miyaura, N.; Suzuki, A. Bull. Chem. Soc. Jpn. 1987, 60, 3471.

  • 2.

    Stereoselective Syntheses of Conjugated 1-Phenylthio-1,3-Alkadienes and 1,3,5-Alkatrienes Through the Palladium-catalyzed Cross-coupling Reaction of (E)- or (Z)-1-Alkenylboronates with (E)- or (Z)-2-Bromo-1-Phenylthio-1-Alkenes

    Ishiyama, T.; Miyaura, N.; Suzuki, A. Chem. Lett. 1987, 25.

  • 1.

    Palladium-catalyzed Cross-coupling Reactions of B-Alkyl-9-BBN or Trialkylboranes with Aryl and 1-Alkenyl Halides

    Miyaura, N.; Ishiyama, T.; Ishikawa, M.; Suzuki, A. Tetrahedron Lett. 1986, 27, 6369.
    DOI: 10.1016/S0040-4039(00)87811-9

Contactus

伊藤 肇 教授

E-mail: hajitoeng.hokudai.ac.jp