石山 竜生

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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+

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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.

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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.

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.

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.

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