Publications | 中尾研究室

Publications

2024

[4] Reductive Homologation of Nitroalkanes via Denitrative Aminoalkylation: Osawa, A.; Balasubramanian, M.; Nakao, Y.
Org. Lett., 2024, 26, 42, 9046-9050.

[3] Magnesiation of Alkyl Fluorides Catalyzed by Rhodium–Aluminum Bimetallic Complexes: Fujii, I.; Higo, R.; Semba, K.; Nakao, Y.
Synlett, 2024, 35, 455-458.

[2] Synthesis and reactivity of Al–Ni bimetallic complexes: Semba, K.; Nagase, K.; Asano, H.; Hara, N.; Nakao, Y.
Polyhedron, 2024, 251, 116823.

[1] Site‐Selective C(sp3)−H Borylation of 3‐Azabicyclo[3.1.0]hexanes by Cooperative Iridium/Aluminum Catalysis: Shimazaki, Y.; Osawa, A.; Nakao, Y.
Asian J. Org. Chem., 2024, 13, e202300487.

2023

[2] An Iridium/Aluminum Cooperative Strategy for the β-C(sp3)–H Borylation of Saturated Cyclic Amines: Kuroda, Y.; Park, K.; Shimazaki, Y.; Zhong, R.-L.; Sakaki, S.; Nakao, Y.
Angew. Chem. Int. Ed., 2023, 62, e202300704.

[1] Catalytic Generation of Radicals from Nitroalkanes: Kashihara, M.; Kosaka, K.; Matsushita, N.; Notsu, S.; Osawa, A.; Nakao, Y.
Synlett, 2023, 34, 1482-1486.

2022

[4] The Kumada–Tamao–Corriu Coupling Reaction Catalyzed by Rhodium–Aluminum Bimetallic Complexes: Fujii, I.; Semba, K.; Nakao, Y.
Org. Lett., 2022, 24, 3075-3079.
Highlighted in Synfacts

[3] Synthesis and Reactivity of Heterobimetallic Co-PAlP Pincer Complexes: Semba, K.; Shimoura, F.; Nakao, Y.
Chem. Lett., 2022, 51, 455-457.

[2] X-Type Aluminyl Ligands for Transition-Metal Catalysis: Hara, N.; Semba, K.; Nakao, Y.
ACS catal., 2022, 12, 1626-1638.

[1] Rh Complex with Unique Rh–Al Direct Bond: Theoretical Insight into its Characteristic Features and Application to Catalytic Reaction via σ-Bond Activation: Li, Q.-Z.; Hara, N.; Semba, K.; Nakao, Y.; Sakaki, S.
Top. Catal., 2022, 65, 392-417.

2021

[11] C2-Selective Alkylation of Pyridines by Rhodium–Aluminum Complexes: Hara, N.; Aso, K.; Li, Q.-Z.; Sakaki, S.; Nakao, Y.
Tetrahedron, 2021, 95, 132339 (special issue).

[10] Synthesis, Electronic Properties, and Lewis Acidity of Rhodium Complexes Bearing X-Type PBP, PAlP, and PGaP Pincer Ligands: Hara, N.; Yamamoto, K.; Tanaka, Y.; Saito, T.; Sakaki, S.; Nakao, Y.
Bull. Chem. Soc. Jpn., 2021, 94, 1859-1868.
Selected as a BCSJ Award Article (open access)

[9] Cross-Coupling Reactions of Nitroarenes: Kashihara, M.; Nakao, Y.
Acc. Chem. Res., 2021, 54, 2928-2935.

[8] Pd-Catalyzed Etherification of Nitroarenes: Matsushita, N.; Kashihara, M.; Formica, M.; Nakao, Y.
Organometallics, 2021, 40, 2209-2214.
Highlighted in Synfacts

[7] 遷移金属／ルイス酸協働触媒によるサイト選択的アレーンC–H官能基化: 中尾佳亮
J. Synth. Org. Chem. Jpn., 2021, 79, 439-448.

[6] C2-Selective Silylation of Pyridines by a Rhodium–Aluminum Complex: Hara, N.; Uemura, N.; Nakao, Y.
Chem. Commun., 2021, 57, 5957-5960.

[5] 1,2-Arylboration ofAliphatic Alkenes by Cooperative Palladium/Copper Catalysis: Semba, K.; Ohtagaki, Y.; Nakao, Y.
Tetrahedron Lett., 2021, 72, 153059 (special issue).

[4] Selective C–O Bond Reduction and Borylation of Aryl Ethers Catalyzed by a Rhodium–Aluminum Heterobimetallic Complex: Seki, R.; Hara, N.; Saito, T.; Nakao, Y.
J. Am. Chem. Soc., 2021, 143, 6388-6394.
highlighted as a spotlight article in JACS

[3] Merging Pd0/PdII Redox and PdII/PdII Non‐redox Catalytic Cycles for the Allylarylation of Electron‐Deficient Alkenes: Semba, K.; Ohta, N.; Paulus, F.; Ohata, M.; Nakao, Y.
Chem. Eur. J., 2021, 27, 5035-5040.

[2] パラジウム触媒を用いた脱ニトロ型カップリング反応の開発: 淺原光太郎; 柏原美勇斗; 武藤慶; 中尾佳亮; 山口潤一郎
J. Synth. Org. Chem. Jpn., 2021, 79, 11-21.

[1] Metal-mediated C–CN Bond Activation in Organic Synthesis: Nakao, Y.
Chem. Rev., 2021, 121, 327-344.

2020

[3] Intramolecular trans‐Carbocarbonation of Carbon‐Carbon Triple Bonds by an anti‐Carbopalladation/Suzuki Coupling Cascade: Reding, A.; Ohta, N.; Sebrantke, P.; Jones, P. G.; Nakao, Y.; Werz, D. B.
ChemCatChem, 2020, 12, 3459-3462.

[2] Magnesiation of Aryl Fluorides Catalyzed by a Rhodium–Aluminum Complex: Fujii, I.; Semba, K.; Li, Q.-Z.; Sakaki, S.; Nakao, Y.
J. Am. Chem. Soc., 2020, 142, 11647-11652.
Highlighted in Synfacts

[1] Nickel-Catalysed anti-Markovnikov Hydroarylation of Unactivated Alkenes with Unactivated Arenes Facilitated by Non-covalent Interactions: Saper, N. I.; Ohgi, A.; Small, D. W.; Semba, K.; Nakao, Y.; Hartwig, J. F.
Nat. Chem., 2020, 12, 276-283.
Highlighted in C&EN

2019

[11] General Principles of Metal/Metal Dual Catalysis: Nakao, Y.
Science of Synthesis: Dual Catalysis in Organic Synthesis, Molander, G. A., Ed.; Thieme: Stuttgart, 2019, 3-8.

[10] A PAlP Pincer Ligand Bearing a 2-Diphenylphosphinophenoxy Backbone: Semba, K.; Fujii, I.; Nakao, Y.
Inorganics, 2019, 7, 140-149.

[9] Catalyst-enabled Site-selectivity in the Iridium-Catalyzed C–H Borylation of Arenes: Kuroda, Y.; Nakao, Y.
Chem. Lett., 2019, 48, 1092-1100.

[8] Pd/NHC-Catalyzed Cross-Coupling Reactions of Nitroarenes: Kashihara, M.; Zhong, R.-L.; Semba, K.; Sakaki, S.; Nakao, Y.
Chem. Commun., 2019, 55, 9291-9294.

[7] Synthesis of N-Heterocyclic Carbene Ligands for Site-Selective C–H Alkylation by Cooperative Nickel/Aluminum Catalysis: Okumura, S.; Ebara, T.; Semba, K.; Nakao, Y.
Heterocycles, 2019, 99, 1128-1144.

[6] Carboallylation of Electron-Deficient Alkenes with Organoboron Compounds and Allylic Carbonates by Cooperative Palladium/Copper Catalysis: Semba, K.; Ohta, N.; Nakao, Y.
Org. Lett., 2019, 21, 4407-4410.

[5] Pd-Catalyzed Denitrative Intramolecular C–H Arylation: Asahara, K. K.; Okita, T.; Saito, A. N.; Muto, K.; Nakao, Y.; Yamaguchi, J.
Org. Lett., 2019, 21, 4721-4724.

[4] meta-Selective C–H Borylation of Benzamides and Pyridines by an Iridium–Lewis Acid Bifunctional Catalyst: Yang, L.; Uemura, N.; Nakao, Y.
J. Am. Chem. Soc., 2019, 141, 7972-7979.

[3] Characterization of Rh–Al Bond in Rh(PAlP) (PAlP = Pincer-type Diphosphino-Aluminyl Ligand) in Comparison with Rh(L)(PMe₃)₂ (L = AlMe₂, Al(NMe₂)₂, BR₂, SiR₃, CH₃, Cl, or OCH₃): Theoretical Insight: Kuriakose, N.; Zheng, J.-J.; Saito, T.; Hara, N.; Nakao, Y.; Sakaki, S.
Inorg. Chem., 2019, 58, 4894-4906.

[2] Cooperative Double Activation Metal/Metal and Metal/Organic Catalysis Enabling Challenging Organic Reactions: Nakao, Y.
Molecular Technology, Volume 4: Synthesis Innovation, Yamamoto, H., Kato, T. Eds; Wiley-VCH, Weinheim, 2019, 95-114.

[1] Cross-Coupling Reactions by Cooperative Pd/Cu or Ni/Cu Catalysis Based on the Catalytic Generation of Organocopper Nucleophiles: Semba, K.; Nakao, Y.
Tetrahedron, 2019, 75, 709-719.

2018

[7] How To Perform Suzuki–Miyaura Reactions of Nitroarene or Nitrations of Bromoarene Using a Pd⁰ Phosphine Complex: Theoretical Insight and Prediction: Zhong, R.-L.; Nagaoka, M.; Nakao, Y.; Sakaki, S.
Organometallics, 2018, 37, 3480-3487.

[6] Carboallylation of Electron-Deficient Alkenes by Palladium/Copper Catalysis: Semba, K.; Ohta, N.; Yano, Y.; Nakao, Y.
Chem. Commun., 2018, 54, 11463-11466.

[5] Aluminum‐Mediated C6‐Selective C−H Alkylation of 2‐Carbamoylbenzofuran by Nickel Catalysis: Okumura, S.; Nakao, Y.
Asian J. Org. Chem., 2018, 7, 1355-1357.

[4] Rhodium Complexes Bearing PAlP Pincer Ligands: Hara, N.; Saito, T.; Semba, K.; Kuriakose, N.; Zheng, H.; Sakaki, S.; Nakao, Y.
J. Am. Chem. Soc., 2018, 140, 7070-7073.

[3] Reductive Denitration of Nitroarenes: Kashihara, M.; Yadav, R. M.; Nakao, Y.
Org. Lett., 2018, 20, 1655-1658.

[2] Hydrogenative Cross-Coupling of Internal Alkynes and Aryl Iodides by Palladium/Copper Cooperative Catalysis: Semba, K.; Kameyama, R.; Nakao, Y.
Chem. Lett., 2018, 47, 213-216.

[1] Site-Selective Linear Alkylation of Anilides by Cooperative Nickel/Aluminum Catalysis: Okumura, S.; Komine, T.; Shigeki, E.; Semba, K.; Nakao, Y.
Angew. Chem. Int. Ed., 2018, 57, 929-932.

2017

[13] Hydroarylation of C–C Multiple Bonds Using Nickel Catalysts: Nakao, Y.
Catalytic Hydroarylation of Carbon-Carbon Multiple Bonds, Ackermann, L., Gunnoe, T. B., Goj Habgood, L. Eds; Wiley-VCH, Weinheim, 2017, 175-192.

[12] Cross-Coupling Reactions by Cooperative Metal Catalysis: Semba, K.; Nakao, Y.
J. Synth. Org. Chem. Jpn., 2017, 75, 1133-1140.

[11] Arylboration of Internal Alkynes by Cooperative Palladium/Copper Catalysis: Semba, K.; Yoshizawa, M.; Ohtagaki, Y.; Nakao, Y.
Bull. Chem. Soc. Jpn., 2017, 90, 1340-1343.

[10] How to Control Inversion vs Retention Transmetalation between Pd^II–Phenyl and Cu^I–Alkyl Complexes: Theoretical Insight: Zheng, H.; Semba, K.; Nakao, Y.; Sakaki, S.
J. Am. Chem. Soc., 2017, 139, 14065-14076.

[9] Buchwald–Hartwig Amination of Nitroarenes: Inoue, F.; Kashihara, M.; Yadav, R. M.; Nakao, Y.
Angew. Chem. Int. Ed., 2017, 56, 13307-13309.
Highlighted in Angew. Chem. Int. Ed.

[8] Aromatic C–H σ-Bond Activation by Ni⁰, Pd⁰, and Pt⁰ Alkene Complexes: Concerted Oxidative Addition to Metal vs Ligand-to-Ligand H Transfer Mechanism: Tang, S.; Eisenstein, O.; Nakao, Y.; Sakaki, S.
Organometallics, 2017, 36, 2761-2771.

[7] Palladium Complexes Bearing Z-type PAlP Pincer Ligands: Saito, T.; Hara, N.; Nakao, Y.
Chem. Lett., 2017, 46, 1247-1249.

[6] The Suzuki–Miyaura Coupling of Nitroarenes: Yadav, R. M.; Nagaoka, M.; Kashihara, M.; Zhong, R.-L.; Miyazaki, T.; Sakaki, S.; Nakao, Y.
J. Am. Chem. Soc., 2017, 139, 9423-9426.
Highlighted in Synfacts
Highlighted in Angew. Chem. Int. Ed.
Featured in Synform

[5] C3-Selective Alkenylation of N-Acylindoles with Unactivated Internal Alkynes by Cooperative Nickel/Aluminium Catalysis: Inoue, F.; Saito, T.; Semba, K.; Nakao, Y.
Chem. Commun., 2017, 53, 4497-4500.

[4] para-Selective C–H Borylation of (Hetero)Arenes by Cooperative Iridium/Aluminum Catalysis: Yang, L.; Semba, K.; Nakao, Y.
Angew. Chem. Int. Ed., 2017, 56, 4853-4857.
Highlighted in Synfacts

[3] Hydroarylation: Nakao, Y.
Science of Synthesis: N-Heterocyclic Carbenes in Catalytic Organic Synthesis Vol. 1, Nolan, S. P., Cazin, C. S. J. Eds; Georg Thieme Verlag KG: Stuttgart•New York, 2017,

[2] para-Selective Alkylation of Sulfonylarenes by Cooperative Nickel/Aluminum Catalysis: Okumura, S.; Nakao, Y.
Org. Lett., 2017, 19, 584-587.

[1] Theoretical Study of Nickel-Catalyzed Selective Alkenylation of Pyridine: Reaction Mechanism and Crucial Roles of Lewis Acid and Ligands in Determining the Selectivity: Singh, V.; Nakao, Y.; Sakaki, S.; Deshmukh, M. M.
J. Org. Chem., 2017, 82, 289-301.

2016

[7] Cooperative Catalysis of Combined Systems of Transition-Metal Complexes with Lewis Acids: Theoretical Understanding: Guan, W.; Zeng, G.; Kameo, H.; Nakao, Y.; Sakaki, S.
Chem. Rec., 2016, 16, 2405-2425.

[6] para-Selective Alkylation of Benzamides and Aromatic Ketones by Cooperative Nickel/Aluminum Catalysis: Okumura, S.; Tang, S.; Saito, T.; Semba, K.; Sakaki, S.; Nakao, Y.
J. Am. Chem. Soc., 2016, 138, 14699-14704.

[5] Arylboration of 1-Arylalkenes by Cooperative Nickel/Copper Catalysis: Semba, K.; Ohtagaki, Y.; Nakao, Y.
Org. Lett., 2016, 18, 3956-3959.
Highlighted in Synfacts

ol-2016-016754_0007

[4] Silicon-based Cross-coupling of Aryl Tosylates by Cooperative Palladium/Copper Catalysis: Ohgi, A.; Semba, K.; Hiyama, T.; Nakao, Y.
Chem. Lett., 2016, 45, 973-975.

[3] Reductive Cross-Coupling of Conjugated Arylalkenes and Aryl Bromides with Hydrosilanes by Cooperative Palladium/Copper Catalysis: Semba, K.; Ariyama, K.; Zheng, H.; Kameyama, R.; Sakaki, S.; Nakao, Y.
Angew. Chem. Int. Ed., 2016, 55, 6275-6279.

[2] C–C Bond Formation by Hetarene C–H Activation: Nakao, Y.
Science of Synthesis: Catalytic Transformations via C–H Activation Vol. 1, Yu, J.-Q. Ed; Georg Thieme Verlag KG: Stuttgart•New York, 2016,

[1] Selective Hydrogenolysis of Arenols with Hydrosilanes by Nickel Catalysis: Ohgi, A.; Nakao, Y.
Chem. Lett., 2016, 45, 45-47.

2015

[6] 19-6-1 有機ケイ素化合物とスズ化合物: 中尾佳亮
有機合成実験法ハントブック　第2版，有機合成化学協会編，丸善出版, 2015,

[5] 19章遷移金属触媒によるカップリング反応: 中尾佳亮
大学院講義有機化学Ⅱ（第2版），野依良治・中筋一弘・玉尾浩平・奈良坂紘一・柴崎正勝・橋本俊一・鈴木啓介・山本陽介・村田道雄編，東京化学同人, 2015,

[4] Anti-Markovnikov Hydroheteroarylation of Unactivated Alkenes with Indoles, Pyrroles, Benzofurans, and Furans Catalyzed by a Nickel-N-Heterocyclic Carbene System: Schramm, Y.; Takeuchi, M.; Semba, K.; Nakao, Y.; Hartwig, J. F.
J. Am. Chem. Soc., 2015, 137, 12215-12218.

[3] Synthesis of Rhazinilam through Intramolecular Arylcyanation of Alkenes Catalyzed Cooperatively by Nickel/Aluminum: Yamada, Y.; Ebata, S.; Hiyama, T.; Nakao, Y.
Tetrahedron, 2015, 71, 4413-4417.

[2] 19章遷移金属触媒によるカップリング反応: 中尾佳亮
ハートウィグ　有機遷移金属化学（下），John F. Hartwig 著，小宮三四郎・穐田宗隆・岩澤伸治訳，東京化学同人, 2015,

[1] Copper-Catalyzed Semihydrogenation of Alkynes to Z-Alkenes: Semba, K.; Kameyama, R.; Nakao, Y.
Synlett, 2015, 26, 318-322.

GA_semba_nakao

2014

[5] 協働金属触媒による炭素-炭素結合形成反応: 中尾佳亮
Organometallic News, 2014, 51-57.

[4] Synthesis of Polysubstituted Benzenes from 2-Pyrone-4,6-dicarboxylic Acid: Okura, K.; Tamura, R.; Shigehara, K.; Masai, E.; Nakamura, M.; Otsuka, Y.; Katayama, Y.; Nakao, Y.
Chem. Lett., 2014, 43, 1349-1351.

CL-140427figc

[3] Arylboration of Alkenes by Cooperative Palladium/Copper Catalysis: Semba, K.; Nakao, Y.
J. Am. Chem. Soc., 2014, 136, 7567-7570.
Highlighted in ACS SELECT (Legacy of Richard Heck)

ja-2014-029556_0010

[2] Intramolecular Aminocyanation of Alkenes by Cooperative Palladium/Boron Catalysis: Miyazaki, Y.; Ohta, N.; Semba, K.; Nakao, Y.
J. Am. Chem. Soc., 2014, 136, 3732-3735.

ja-2013-122632_0008

[1] Catalytic C–CN Bond Activation: Nakao, Y.
Top. Curr. Chem., 2014, 346, 33-58.