久保田 浩司 論文リスト


List of publication

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[52] Mechanochemical Protocol Facilitates the Generation of Arylmanganese Nucleophiles from Unactivated Manganese Metal
Takahashi, R.; Gao, P.; Kubota, K.*; Ito, H.* Chem. Rxiv. 2022,
DOI: 10.26434/chemrxiv-2022-48bnj

[51] Stereospecific Synthesis of Silicon-Stereogenic Optically Active Silylboranes and their Application to Synthesis of Chiral Organosilanes
Wang, X.; Feng, C.; Kubota, K.*; Ito, H.* Chem. Rxiv. 2022,
DOI: 10.26434/chemrxiv-2022-ft3c6

[50] Cu(I)-Catalyzed Enantioselective γ-Boryl Substitution of Trifluoromethyl- and Silyl-substituted Alkenes
Oyama, N.; Akiyama, S.; Kubota, K.; Imamoto, T.; Ito, H.* Eur. J. Org. Chem. 2022, e202200664.
DOI: 10.1002/ejoc.202200664

[49] Mechanochemically Generated Calcium-Based Heavy Grignard Reagents and Their Application to Carbon−Carbon Bond-Forming Reactions
Gao, P.; Jiang, J.; Maeda, S.; Kubota, K.*; Ito, H.* Angew. Chem. Int. Ed. 2022, Just Accepted
DOI: 10.1002/anie.202207118

[48] 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

[47] Solid-state cross-coupling reactions of insoluble aryl halides under polymer-assisted grinding conditions
Kubota, K.*; Seo, T.; Ito, H.* Faraday Discuss. 2022, Just Accepted
DOI: 10.1039/D2FD00121G

[46] Insight into the Reactivity Profile of Solid-State Aryl Bromides in Suzuki-Miyaura Cross-Coupling Reactions Using Ball Milling
Kubota, K.*; Kondo, K.; Seo, T.; Ito, H.* Synlett 2022, 33, 898 - 902.
DOI: 10.1055/a-1748-3797

[45] Efficient Access to Materials-Oriented Aromatic Alkynes via the Mechanochemical Sonogashira Coupling of Solid Aryl Halides with Large Polycyclic Conjugated Systems
Gao, Y.; Feng, C.; Seo, T.; Kubota, K.*; Ito, H.* Chem. Sci. 2022, 13, 430 - 438.
DOI: 10.1039/D1SC05257H

[44] Solid-State C−N Cross-Coupling Reactions with Carbazoles as Nitrogen Nucleophiles Using Mechanochemistry
Kubota, K.*; Endo, T.; Uesugi, M.; Hayashi, Y.; Ito, H.* ChemSusChem 2022, 15, e202102132.
DOI: 10.1002/cssc.202102132

[43] Palladium-Catalyzed Solid-State Polyfluoroarylation of Aryl Halides Using Mechanochemistry
Takahashi, R.; Seo, T.; Kubota, K.*; Ito, H.* ACS Catal. 2021, 11, 14803 - 14810.
DOI: 10.1021/acscatal.1c03731

[42] Mechanochemical synthesis of magnesium-based carbon nucleophiles in air and their use in organic synthesis
Takahashi, R.; Hu, A.; Gao, P.; Gao, Y.; Pang, Y.; Seo, T.; Maeda, S.; Jiang, J.; Takaya, H.; Kubota, K.*; Ito, H.* Nature Commun. 2021, 12, 6691.
DOI: 10.1038/s41467-021-26962-w

[41] Synthesis of Hydrosilylboronates via the Monoborylation of a Dihydrosilane Si−H Bond and Their Application for the Generation of Dialkylhydrosilyl Anions
Takeuchi, T.; Shishido, R.; Kubota, K.*; Ito, H.* Chem. Sci. 2021, 12, 11799 - 11804.
DOI: 10.1039/D1SC01440D

[40] Synthesis of Chiral α-Amino Tertiary Boronates via the Catalytic Enantioselective Nucleophilic Borylation of Dialkyl Ketimines
Kubota, K.*; Miura, D.; Takeuchi, T.; Osaki, S.; Ito, H.* ACS Catal. 2021, 11, 6733 - 6740.
DOI: 10.1021/acscatal.1c01689

[39] Introduction of a Luminophore into Generic Polymers via Mechanoradical Coupling with a Prefluorescent Reagent
Kubota, K.*; Toyoshima, N.; Miura, D.; Jiang, J.; Maeda, S.; Jin, M.*; Ito, H.* Angew. Chem. Int. Ed. 2021, 60, 16003 - 16008.
DOI: 10.1002/anie.202105381

[38] Tackling Solubility Issues in Organic Synthesis: Solid-State Cross-Coupling of Insoluble Aryl Halides
Seo, T.; Toyoshima, N; Kubota, K.*; Ito, H.* J. Am. Chem. Soc. 2021, 143, 6165 - 6175.
DOI: 10.1021/jacs.1c00906

[37] A Copper(I)-Catalyzed Radical Relay Reaction Enabling the Intermolecular 1,2-Alkylborylation of Unactivated Olefins
Akiyama, S.; Oyama, N.; Endo, T.; Kubota, K.; Ito, H.* J. Am. Chem. Soc. 2021, 143, 5260 - 5268.
DOI: 10.1021/jacs.1c02050

[36] Copper(I)-Catalyzed Stereoselective Silylative Dearomatization of Indoles and Pyrroles using Silylboronates
Hayama, K.; Takahashi, Rikuro.; Kubota, K.; Ito, H.* Chem. Lett. 2021, 50, 289 - 292.
DOI: 10.1246/cl.200725

[35] A Glove-box- and Schlenk-line-free Protocol for Solid-state C-N Cross-coupling Reactions Using Mechanochemistry
Kubota, K.*; Takahashi, R.; Uesugi, M.; Ito, H.* ACS Sustainable Chem. Eng. 2020, 8, 16577 - 16582.
DOI: 10.1021/acssuschemeng.0c05834

[34] Solid-State Radical C−H Trifluoromethylation Reactions Using Ball Milling and Piezoelectric Materials
Pang, Y.; Lee, J. W.; Kubota, K.*; Ito, H.* Angew. Chem. Int. Ed. 2020, 59, 22570 - 22576.
DOI: 10.1002/anie.202009844
This is our second paper for mechanoredox reaction. See also, https://science.sciencemag.org/content/366/6472/1500

[33] 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

[32] Selective Mechanochemical Monoarylation of Unbiased Dibromoarenes by In-situ Crystallization
Seo, T.; Kubota, K.*; Ito, H.* J. Am. Chem. Soc. 2020, 142, 9884 - 9889.
DOI: 10.1021/jacs.0c01739
Under ball milling reaction conditions, palladium-catalyzed Suzuki–Miyaura cross-coupling reactions of unbiased dibromoarenes selectively afford the monoarylated products. This study gives a new approach that uses in-situ structure transitions in solids to achieve selective organic transformations difficult with traditional solution-based synthesis.

[31] Copper(I)-Catalyzed Boryl Substitution of 1-Trifluoromethyl Allenes for the Synthesis of 3-Boryl-Substituted 1,1-gem-Difluorodienes
Akiyama, S.; Nomura, S; Kubota, K.; Ito, H.* J. Org. Chem. 2020, 85, 4172 - 4181.
DOI: 10.1021/acs.joc.9b03353
A method to synthesize 3-boryl-1,1-gem-difluorodienes via the copper(I)-catalyzed boryl substitution of trifluoromethyl-substituted allenes was developed. The borylated compounds were obtained up to 91% yield with excellent selectivity. We proposed that the reaction proceeded via γ-selective borylcupration into the trifluoromethyl-substituted allene, followed by copper(I)-β-fluoro elimination. Subsequent transformations of the borylation product by Suzuki–Miyaura cross-coupling or Diels–Alder reaction provided various compounds bearing a difluoro moiety, which are difficult to synthesize by existing methods.

[30] Synthesis of Chiral N-Heterocyclic Allylboronates via the Enantioselective Borylative Dearomatization of Pyrroles
Hayama, K.; Kojima, R.; Kubota, K.; Ito, H.* Org. Lett. 2020, 22, 739 - 744.
DOI: 10.1021/acs.orglett.9b04581

[29] Air- and moisture-stable Xantphos-ligated palladium dialkyl complex as a precatalyst for cross-coupling reactions
Takahashi, R.; Kubota, K.*; Ito, H.* Chem. Commun. 2020, 56, 407 - 410.
DOI: 10.1039/C9CC06946A

[28] Redox Reactions of Small Organic Molecules Using Ball Milling and Piezoelectric Materials
Kubota, K.*; Pang, Y.; Miura, A.; Ito, H.* Science 2019, 366, 1500 - 1504.
DOI: 10.1126/science.aay8224

[27] 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

[26] Catalytic Enantioselective Synthesis of Allylic Boronates Bearing a Trisubstituted Alkenyl Fluoride and Related Derivatives
Akiyama, S.; Kubota, K.; Mikus, M. S.; Paioti, P. H. S.; Romiti, F.; Liu, Q.; Zhou, Y.; Hoveyda, A. H.*; Ito, H.* Angew. Chem. Int. Ed. 2019, 58, 11998 - 12003.
DOI: 10.1002/anie.201906283


Highlighted as a Frontispiece in Issue 35, 2019

[25] Copper(I)-Catalyzed Enantioconvergent Borylation of Racemic Benzyl Chlorides Enabled by Quadrant-by-Quadrant Structure Modulation of Chiral Bisphosphine Ligands
Iwamoto, H.; Endo, K.; Ozawa, Y.; Watanabe, Y.; Kubota, K.; Imamoto, T.; Ito, H.* Angew. Chem. Int. Ed. 2019, 58, 11112 - 11117.
DOI: 10.1002/anie.201906011

[24] Synthesis of 2-alkyl-2-boryl-substituted-tetrahydrofurans via copper(I)-catalysed borylative cyclization of aliphatic ketones
Kubota, K.; Uesugi, M.; Osaki, S.; Ito, H.* Org. Biomol. Chem. 2019, 17, 5680 - 5683.
DOI: 10.1039/C9OB00962K

[23] Mechanochemistry allows carrying out sensitive organometallic reactions in air: Glove-box-and-Schlenk-line-free synthesis of oxidative addition complexes from aryl halides and palladium(0)
Kubota, K.*; Takahashi, R.; Ito, H.* Chem. Sci. 2019, 10, 5837 - 5842.
DOI: 10.1039/C9SC01711A

[22] 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

[21] Olefin-accelerated solid-state C–N cross-coupling reactions using mechanochemistry
Kubota, K.*; Seo, T.; Koide, K.; Hasegawa, Y.; Ito, H.* Nature Communications 2019, 10, 111.
DOI: 10.1038/s41467-018-08017-9
https://www.nature.com/articles/s41467-018-08017-9 ・北海道大学 PRESS RELEASE 固体状態で進行するクロスカップリング反応を開発 Behind the Paper (Nature Research Chemistry Community) Cross-Coupling in Solid Using MechanochemistryHighlighted in News Paper: 日経産業新聞20190111 ・Highlighted in News Paper: 日刊工業新聞20190115 ・Highlighted in News Web: NHK 北大 医薬品合成で新手法開発 Highlighted in News Web: 環境展望台 北大 固体状態で進行する有機合成反応プロセスを開発Selected as "Nature Communications Editor's Highlights"Highlighted in Phys.org.: Boosting solid state chemical reactionsHighlighted in Converter News: Olefin Enables Efficient Solvent-Free Cross-Coupling ReactionsHighlighted in Technology Networks: Olefin Makes Chemistry GreenerHighlighted in Chem Station: スポットライトリサーチ ”メカノケミストリーを用いた固体クロスカップリング反応"

[20] Copper(I)-Catalyzed Stereoselective Defluoroborylation of Aliphatic Gem-Difluoroalkenes
Ito, H.*; Seo, T.; Kojima, R.; Kubota, K. Chem. Lett. 2018, 47, 1330 - 1332.
DOI: 10.1246/cl.180656

[19] Enantioselective Synthesis of N,S-Acetals by an Oxidative Pummerer Type Transformation Using Phase-Transfer Catalysis
Biswas, S.; Kubota, K.; Orlandi, M.; Turberg, M.; Miles, D. H.; Sigman, M. S.; Toste, F. D. Angew. Chem. Int. Ed. 2018, 57, 589 - 593.
DOI: 10.1002/anie.201711277

[18] Palladium Oxidative Addition Complexes for Peptide and Protein Crosslinking
Kubota, K.; Dai, P.; Pentelute B. L.; Buchwald S. L. J. Am. Chem. Soc. 2018, 140, 3128 - 3133.
DOI: 10.1021/jacs.8b00172

[17] Copper(I)-Catalyzed Diastereoselective Dearomative Carboborylation of Indoles
Hayama, K.; Kubota, K.; Iwamoto, H.; Ito, H.* Chem. Lett. 2017, 46, 1800 - 1802.
DOI: 10.1246/cl.170825

[16] Copper(I)-Catalyzed Regio- and Stereoselective Intramolecular Alkylboration of Propargyl Ethers and Amines
Iwamoto, H.; Ozawa, Y.; Kubota, K.; Ito, H.* J. Org. Chem. 2017, 82, 10563 - 10573.
DOI: 10.1021/acs.joc.7b02071

[15] Stereodivergent Hydrodefluorination of gem-Difluoroalkenes: Selective Synthesis of (Z)- and (E)-Monofluoroalkenes
Kojima, R.; Kubota, K.; Ito, H.* Chem. Commun. 2017, 53, 10688 - 10691.
DOI: 10.1039/C7CC05225A

・Highlighted in Synfacts 2018, 14, 55. DOI: 10.1055/s-0036-1591076

[14] Copper(I)-Catalyzed Enantioselective Nucleophilic Borylation of Ketones: Synthesis of Enantioenriched Chiral Tertiary alpha-Hydroxyboronates
Kubota, K.; Osaki, S.; Jin, M.; Ito, H.* Angew. Chem. Int. Ed. 2017, 56, 6646 - 6650.
DOI: 10.1002/anie.201702826


・Highlighted in Synfacts 201713, 745. DOI: 10.1055/s-0036-1590558

[13] Synthesis of Enantiomerically Enriched Chiral Tetrahydroquinolines via Sequential Dearomatization/Enantioselective Borylation Reactions
Kubota, K.; Watanabe, Y.; Ito, H.* Adv. Synth. Catal. 2016, 358, 15, 2379 - 2384.
DOI: 10.1002/adsc.201600372


[12] Computational Insight into the Enantioselective Nucleophilic Borylation of a Polarized C=O Double Bond Catalyzed by Di-phosphine-Borylcopper(I) Complexes
Kubota, K.; Jin, M.; Ito, H.* Organometallics 2016, 35, 1376 - 1383.
DOI: 10.1021/acs.organomet.5b00621



[11] Enantioselective Synthesis of Chiral Piperidines via the Stepwise Dearomatization/Borylation of Pyridines
Kubota, K.; Watanabe, Y.; Hayama, K.; Ito, H.* J. Am. Chem. Soc. 2016, 138, 13, 4338 - 4341.
DOI: 10.1021/jacs.6b01375


[10] Highly Selective Markovnikov Hydroboration of Alkyl-Substituted Terminal Alkenes with a Phosphine-Copper(I) Catalyst
Iwamoto, H.; Kubota, K.; Ito, H. Chem. Commun. 2016, 5916 - 5919.
DOI: 10.1039/C6CC00782A

MHB_GA_1 (1)   iwamoto_cover
Highlighted as a Back Cover in Issue 35, 2016

[9] Copper(I)-Catalyzed Diastereoselective Borylative Exo-Cyclization of Alkenyl Aryl Ketones
Yamamoto, E.; Kojima, R.; Kubota, K.; Ito, H. Synlett 2015, 27, 2, 272 - 276.
DOI: 10.1055/s-0035-1560721

[8] Enantioselective Borylative Dearomatization of Indoles through Copper(I) Catalysis
Kubota, K.; Hayama, K.; Iwamoto, H.; Ito, H. Angew. Chem. Int. Ed. 2015, 54, 8809 - 8813.
DOI: 10.1002/anie.201502964


・Highlighted in Synfacts 2015, 11, 840. DOI: 10.1055/s-0034-1381153

[7] Copper(I)-Catalyzed Carbon–Halogen Bond-Selective Boryl Substitution of Alkyl Halides Bearing Terminal Alkene Moieties
Iwamoto, H.; Kubota, K.; Yamamoto, E; Ito, H. Chem. Comm. 2015, 51, 9655 - 9658.
DOI: 10.1039/C5CC02760H

[6] Reaction Optimization, Scalability, and Mechanistic Insight on the Catalytic Enantioselective Desymmetrization of 1,1-Diborylalkanes via Suzuki–Miyaura Cross-Coupling
Sun, H.; Kubota, K.; Hall, D. G. Chem. Eur. J. 2015, Early View
DOI: doi/10.1002/chem.201406680


[5] Silicon-Tethered Strategy for Copper(I)-Catalyzed Stereo- and Regioselective Alkylboration of Alkynes
Kubota, K.; Iwamoto, H.; Yamamoto, E; Ito, H. Org. Lett. 2015, 17, 620 - 623.
DOI: 10.1021/ol503620n


・Highlighted in Synfacts 2015, 11, 406. DOI: 10.1055/s-0034-1380388


[4] Copper(I)-Catalyzed Enantioselective Nucleophilic Borylation of Aldehydes: An Efficient Route to Enantiomerically Enriched α-Alkoxyorganoboronate Esters
Kubota, K.; Yamamoto, E.; Ito, H. J. Am. Chem. Soc. 2015, 137, 1, 420 - 424.
DOI: 10.1021/ja511247z


・Highlighted in Synfacts 2015, 11, 286. DOI: 10.1055/s-0034-1380053

[3] Regio- and Enantioselective Monoborylation of Alkenylsilanes Catalyzed by an Electron-Donating Chiral Phosphine-opper(I) Complex
Kubota, K.; Yamamoto, E.; Ito, H. Advanced Synthesis & Catalysis 2013, 355, 3527 - 3531.
DOI: 10.1002/adsc.201300765


・Highlighted in Synfacts, 2013, 10, 284. DOI: 10.1055/s-0033-1340694

[2] Copper(I)-Catalyzed Borylative Exo-Cyclization of Alkenyl Halides Containing Unactivated Double Bond
Kubota, K.; Yamamoto, E.; Ito, H. J. Am. Chem. Soc. 2013, 135, 2635 - 2640.
DOI: 10.1021/ja3104582


[1] Copper(I)-Catalyzed Boryl Substitution of Unactivated Alkyl Halides
Ito, H.; Kubota, K. Org. Lett. 2012, 14, 890 - 893.
DOI: 10.1021/ol203413w


TOC表示: あり | なし

[4] Mechanochemical cross-coupling reactions
Kubota, K.*; Ito, H.* Trends Chem. 2020, Just Accepted
DOI: 10.1016/j.trechm.2020.09.006

[3] Formal Nucleophilic Borylation and Borylative Cyclization of Organic Halides
Kubota, K.; Iwamoto, H.; Ito, H.* Org. Biomol. Chem. 2017, 15, 285 - 300.
DOI: 10.1039/C6OB02369J

OBC review

• Selected as the most cited and accessed articles published in Organic & Biomolecular Chemistry (OBC) in 2017.

[2] Topochemical Photocyclizations for the Synthesis of Two-Dimensional Polymers
Kubota, K. J. Synth. Org. Chem. Jpn. 2014, 72, 834.
DOI: 10.5059/yukigoseikyokaishi.72.834

[1] Selective Synthesis of Organoboron Compounds with Copper(I)-Phosphine Complex Catalysts
Yamamoto, E.; Takenouchi, Y.; Kubota, K.; Ito, H. J. Synth. Org. Chem. Jpn. 2014, 72, 758 - 769.
DOI: 10.5059/yukigoseikyokaishi.72.758