Original Papers:
 

​"BN-Embedded Aromatic Hydrocarbon Synthesis via Nucleophilic Diboration Reactions"

Mei Harada, Shota Fujioka, Shoma Ansai, Chao Wang, Shinichiro Kamino, Keiichi Hirano,* Masanobu Uchiyama*

Org. Lett. 2024, 26, 247–251.

DOI: 10.1021/acs.orglett.3c03898

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​"Perfluoroalkoxylation Reaction via Dual Concurrent Catalysis"

Shota Fujioka, Keiichi Hirano,* Naoyuki Hoshiya, Akiyoshi Yamauchi, Yousuke Kishikawa, Masanobu Uchiyama*

Chem. Commun. 2023, 59, 8290-8293.

DOI: 10.1039/D3CC02485G

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"Lithium Aryltrifluorobotare as a Catalyst for Halogen Transfer"

Kengo Inoue, Keiichi Hirano,* Shota Fujioka, Masanobu Uchiyama,* Atsunori Mori, Kentaro Okano*

ACS Catal. 2023, 13, 3788-3793.

DOI: 10.1021/acscatal.2c06082

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"Practical and Facile Access to Bicyclo[3.1.1]heptanes: Potent Bioisosteres of meta-Substituted Benzenes"

Toranosuke Iida, Junichiro Kanazawa,* Tadafumi Matsunaga, Kazunori Miyamoto, Keiichi Hirano,* Masanobu Uchiyama*

J. Am. Chem. Soc. 2022, 144, 21848-21852.

DOI: 10.1021/jacs.2c09733

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"Nucleophilic Activation of Hydrosilanes via a Strain-imposing Strategy Leading to Functional Sila-aromatics"

Toshiya Ikeuchi, Keiichi Hirano,* Masanobu Uchiyama*

J. Am. Chem. Soc. 2021, 143, 4879-4885.

DOI: 10.1021/jacs.0c12619

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"Nucleophilic Diboration Strategy Targeting Diversified 1-Boraphenarene Architectures"

Keiichi Hirano,* Kensuke Morimoto, Shota Fujioka, Kazunori Miyamoto, Atsuya Muranaka, Masanobu Uchiyama*

Angew. Chem. Int. Ed. 2020, 59, 21448-21453.

DOI: 10.1002/anie.202009242

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"Intramolecular Benzyne-Phenolate [4+2] Cycloadditions"

Hiroshi Takikawa, Arata Nishii, Hiromu Takiguchi, Hirotoshi Yagishita, Masato Tanaka, Keiichi Hirano, Masanobu Uchiyama, Ken Ohmori,* Keisuke Suzuki*

Angew. Chem. Int. Ed. 2020, 59, 12440-12444.

DOI: 10.1002/anie.202003131

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"Lipshutz-type Bis(amido)argentates for Directed Argentation"

Noriyuki Tezuka,* Keiichi Hirano,* Andrew J. Peel, Andrew E. H. Wheatley, Kazunori Miyamoto, Masanobu Uchiyama*

Chem. Sci. 2020, 11, 1855-1861.

DOI: 10.1039/c9sc06060j

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"A Direct, Chemo-, and Regioselective Cross-Coupling Reaction of Arenes  Sequential Directed  Cupration and Oxidation"

Noriyuki Tezuka, Keiichi Hirano,* Masanobu Uchiyama*

Org. Lett. 2019, 21, 9536-9540.

DOI: 10.1021/acs.orglett.9b03719

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"Alkynylboration Reactions Leading to Boron-containing π-Extended -Stilbenes as a Highly Tunable Fluorophore"

Marina Nogami, Keiichi Hirano,* Kensuke Morimoto, Masaru Tanioka, Kazunori Miyamoto, Atsuya Muranaka, Masanobu Uchiyama*

Org. Lett. 2019, 21, 3392-3395.

DOI: 10.1021/acs.orglett.9b01132

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"Diaryl-λ3-chloranes: Versatile Synthesis and Unique Reactivity as Aryl Cation Equivalent"

Misuzu Nakajima, Kazunori Miyamoto,* Keiichi Hirano, Masanobu Uchiyama*​​

J. Am. Chem. Soc. 2019, 141, 6499-6503.

DOI: 10.1021/jacs.9b02436

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"Mechanistic Study on Aryl Exchange Reaction of Diaryl-λ3-iodane with Aryl Iodide"

Yui Masumoto, Kazunori Miyamoto,* Takuto Iuchi, Masahito Ochiai, Keiichi Hirano, Tatsuo Saito, Chao Wang, Masanobu Uchiyama*

J. Org. Chem. 2018, 83, 289-295.

DOI: 10.1021/acs.joc.7b02701

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"Iodoarene-catalyzed Oxidative Transformations Using Molecular Oxygen"

​Kazunori Miyamoto,* Junpei Yamashita, Shodai Narita, Yuuta Sakai, Keiichi Hirano, Tatsuo Saito, Chao Wang, Masahito Ochiai, Masanobu Uchiyama*

Chem. Commun. 2017, 53, 9781-9784.

DOI: 10.1039/c7cc05160c

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"Transition Metal-Free trans-Selective Alkynylboration of Alkynes"

Marina Nogami, Keiichi Hirano,* Misae Kanai, Chao Wang, Tatsuo Saito, Kazunori Miyamoto, Atsuya Muranaka, Masanobu Uchiyama*

J. Am. Chem. Soc. 2017, 139, 12358-12361.

DOI: 10.1021/jacs.7b06212

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"Rhodium-catalyzed (Perfluoroalkyl)olefination of Acetanilides Leading to Perfluoroalkylated Aromatics"

​Kohei Harada, Noriyuki Tezuka, Keiichi Hirano,* Kazunori Miyamoto, Tatsuo Saito, Masanobu Uchiyama*

Chem. Pharm. Bull. 2016, 64, 1442-1444.

DOI: 10.1248/cpb.c16-00588

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"Direct Hydroxylation and Amination of Arenes Deprotonative Cupration"

Noriyuki Tezuka, Kohei Shimojo, Keiichi Hirano,* Shinsuke Komagawa, Kengo Yoshida, Chao Wang, Kazunori Miyamoto, Tatsuo Saito, Ryo Takita, Masanobu Uchiyama*

J. Am. Chem. Soc. 2016, 138, 9166–9171.

DOI: 10.1021/jacs.6b03855

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"Gold-Catalyzed Annulation of Alkyne Alcohols: Regioselective Construction of Functionalized 6,6- and 6,7-Bicyclic Ethers"

Mio Kubota, Tatsuo Saito,* Kazunori Miyamoto, Keiichi Hirano, Chao Wang, Masanobu Uchiyama*

Chem. Pharm. Bull. 2016, 64, 845-855.

DOI: 10.1248/cpb.c16-00204

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"Allylic Borylation of Tertiary Allylic Alcohols: A Divergent and Straightforward Access to Allylic Boronates"

Kohei Harada, Marina Nogami, Keiichi Hirano,* Daisuke Kurauchi, Hisano Kato, Kazunori Miyamoto, Tatsuo Saito, Masanobu Uchiyama*

Org. Chem. Front. 2016, 3, 565-569.

DOI: 10.1039/C6QO00009F

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"Dialkylzinc-Mediated Allylic Polyfluoroarylation Reaction"

Daisuke Kurauchi, Keiichi Hirano,* Hisano Kato, Tatsuo Saito, Kazunori Miyamoto, Masanobu Uchiyama*

Tetrahedron 2015, 71, 5849-5857.

DOI: 10.1016/j.tet.2015.05.107

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"Perfluoroalkyl and -aryl Zinc Ate Complexes: Generation, Reactivity, and Synthetic Application"

Xuan Wang, Keiichi Hirano,* Daisuke Kurauchi, Hisano Kato, Naoyuki Toriumi, Ryo Takita, Masanobu Uchiyama*

Chem. Eur. J. 2015, 21, 10993-10996.

DOI: 10.1002/chem.201501811

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"Highly Chemoselective and Versatile Method for Direct Conversion of Carboxylic Acids to Ketones Utilizing Zinc Ate Complexes"

Ryo Murata, Keiichi Hirano,* Masanobu Uchiyama*

Chem. Asian J. 2015, 10, 1286-1290.

DOI: 10.1002/asia.201500308

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"Dialkylzinc-Mediated Cross-Coupling Reactions of Perfluoroalkyl and Perfluoroaryl Halides with Aryl Halides"

Hisano Kato, Keiichi Hirano,* Daisuke Kurauchi, Naoyuki Toriumi, Masanobu Uchiyama*

Chem. Eur. J. 2015, 21, 3895-3900.

DOI: 10.1002/chem.201406292

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"Trans-Diborylation of Alkynes: Pseudo-Intramolecular Strategy Utilizing Propargylic Alcohol Unit"

Yuki Nagashima, Keiichi Hirano,* Ryo Takita, Masanobu Uchiyama*

J. Am. Chem. Soc. 2014,136, 8532–8535.

DOI: 10.1021/ja5036754

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"18π Tautomeric Benziphthalocyanine: A Functional Near-IR Dye with Tunable Aromaticity"

Naoyuki Toriumi, Atsuya Muranaka,* Keiichi Hirano, Kengo Yoshida, Daisuke Hashizume, Masanobu Uchiyama*

Angew. Chem. Int. Ed. 2014, 53, 7814-7818.

DOI: 10.1002/anie.201404020

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"Design, Generation, and Synthetic Application of Borylzincate: Borylation of Aryl Halides and Borylzincation of Benzynes/Terminal Alkyne"

Yuki Nagashima, Ryo Takita,* Kengo Yoshida, Keiichi Hirano, Masanobu Uchiyama*

J. Am. Chem. Soc. 2013, 135, 18730–18733.

DOI: 10.1021/ja409748m

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"Amidocuprates for Directed Cupration: Structural Study, Mechanistic Investigation, and Chemical Requirements"

Shinsuke Komagawa,* Shinya Usui, Joanna Haywood, Philip J. Harford, Andrew E. H. Wheatley, Yotaro Matsumoto, Keiichi Hirano, Ryo Takita, Masanobu Uchiyama*

Angew. Chem. Int. Ed. 2012, 51, 12081-12085.

DOI: 10.1002/anie.201204923

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"Dinuclear Zinc Catalyzed Asymmetric Spirannulation Reaction: An Umpolung Strategy for Formation of α-Alkylated-α-Hydroxyoxindoles"

Barry M. Trost,* Keiichi Hirano

Org. Lett. 2012, 14, 2446-2449.

DOI: 10.1021/ol300577y

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"A Family of Thiazolium Salt Derived N-Heterocyclic Carbenes (NHCs) for Organocatalysis: Synthesis, Investigation and Application in Cross-Benzoin Condensation"

Isabel Piel, Marius D. Pawelczyk, Keiichi Hirano, Roland Fröhlich, Frank Glorius*

Eur. J. Org. Chem. 2011, 5475-5484.

DOI: 10.1002/ejoc.201100870

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"Stereoselective Synthesis of α-Alkyl-α-Hydroxycarboxylic acid Derivatives Catalyzed by a Dinuclear Zinc Complex"

Barry M. Trost,* Keiichi Hirano

Angew. Chem. Int. Ed. 2012, 51, 6480-6483.

DOI: 10.1002/anie.201201116

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"Highly Asymmetric NHC-Catalyzed Hydroacylation of Unactivated Alkenes and Mechanistic Insight"

Isabel Piel, Marc Steinmetz, Keiichi Hirano, Roland Fröhlich, Stefan Grimme,* Frank Glorius*

Angew. Chem. Int. Ed. 2011, 50, 4983-4987.

DOI: 10.1002/anie.201008081

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"Copper-Catalyzed Synthesis of 2-Unsubstituted, N-Substituted Benzimidazoles"

Keiichi Hirano, Biju T. Akkattu, F. Glorius*

J. Org. Chem. 2009, 74, 9570-9572.

DOI: 10.1021/jo902160y

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"NHC-Catalyzed Hydroacylation of Unactivated Double Bonds"

Keiichi Hirano, Biju T. Akkattu, Isabel Piel, Frank Glorius*

J. Am. Chem. Soc. 2009, 131, 14190-14191.

DOI: 10.1021/ja906361g

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"Switching the Electron-Donor Properties of N-Heterocyclic Carbenes by a Facile Deprotonation Strategy"

Biju T. Akkattu, Keiichi Hirano, Roland Fröhlich, Frank Glorius*

Chem. Asian J. 2009, 4, 1786-1789.

DOI: 10.1002/asia.200900410

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"A Modular Synthesis of Highly Substituted Imidazolium Salts"

Keiichi Hirano,§ Slawomir Urban,§ Congyang Wang, Frank Glorius*

Org. Lett. 2009, 11, 1019-1022. § Both authors contributed equally to this work.

DOI: 10.1021/ol8029609

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"Palladium-Catalyzed C-Allylation of Benzoins & an NHC-Catalyzed Three Component Coupling Derived Thereof: Compatibility of NHC- and Pd-Catalysts"

Raphaël Lebeuf,§ Keiichi Hirano,§ Frank Glorius*

Org. Lett. 2008, 10, 4243-4246. § Both authors contributed equally to this work.

DOI: 10.1021/ol801644f

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"Diastereoselective Synthesis of Trifluoromethylated γ-Butyrolactones via N-Heterocyclic Carbene-Catalyzed Conjugated Umpolung of α,β-Unsaturated Aldehydes"

Keiichi Hirano, Isabel Piel, Frank Glorius*

Adv. Synth. Catal. 2008, 350, 984-988.

DOI: 10.1002/adsc.200800051

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"ALLYLBORONATION OF IMINES: 1-PHENYLHEX-5-EN-3-AMINE"

Masaharu Sugiura, Keiichi Hirano, Shu Kobayashi*

Org. Synth. 2006, 83, 170-176.

DOI: 10.1002/0471264229.os083.22

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"α-Aminoallylation of Aldehydes in Aqueous Ammonia"

Shu Kobayashi,* Keiichi Hirano, Masaharu Sugiura

Chem. Commun. 2005, 104-105.

DOI: 10.1039/b415264f

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"Direct Synthesis of Unprotected α-Amino Acids via Allylation of Hydroxyglycine"

Masaharu Sugiura, Chieko Mori, Keiichi Hirano, Shu Kobayashi*

Can. J. Chem. 2005, 83, 937-942.

DOI: 10.1139/v05-096

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"α-Aminoallylation of Aldehydes with Ammonia: Stereoselective Synthesis of Homoallylic Primary Amines"

Masaharu Sugiura, Keiichi Hirano, Shu Kobayashi*

J. Am. Chem. Soc. 2004, 126, 7182-7183.

DOI: 10.1021/ja049689o

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