Original Article

2024

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Asymmetric Synthesis of SCF3-Substituted Alkylboronates by Copper-Catalyzed Hydroboration of 1-Trifluoromethylthioalkenes
Y. Kojima, Y. Nishii, K. Hirano
Angew. Chem. Int. Ed. 2024, accepted. [Link]

Pd-catalysed C-H alkynylation of benzophospholes
Y. Tokura, S. Xu, K. Yasui, Y. Nishii, K. Hirano
Chem. Commun. 2024, accepted [Link]

Tunable Mechanochromic Luminescence of Benzofuran-Fused Pyrazine: Effects of Alkyl Chain Length and Branching Pattern
S. Nakamura, K. Okubo, Y. Nishii, K. Hirano, N. Tohnai, M. Miura
J. Mater. Chem. C 2024, 12, 2370-2378. [Link]

Direct synthesis of spirobifluorenes by formal dehydrative coupling of biaryls and fluorenones
Y. Kato, K. Nishimura, Y. Nishii, K. Hirano
Chem. Sci. 2024, accepted [Link]

Aromatic halogenation using carborane catalyst
C. N. Kona, R. Oku, S. Nakamura, M. Miura, K. Hirano, Y. Nishii
Chem 2024, 10, 402-413. [Link] Early version in ChemRxiv [Link]
大阪大学プレスリリースReSOU [Link]

2023

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Palladium-Catalyzed α-Selective Halogenation of Triptycene Using Sulfur Directing Group
K. Ueno, Y. Nishii, K. Hirano, M. Miura
Asian J. Org. Chem. 2023, e202300588. [Link]

Rhodium-Catalyzed Direct Vinylene Annulation of 2-Aryloxazoline and Cascade Ring-Opening Using Vinyl Selenone
J. Kitano, Y. Nishii, K. Hirano, M.Miura
Synlett 2023 accepted [Link]

Synthesis of Axially Chiral Bibenzo[g]coumarin Derivatives by Rhodium-Catalyzed Oxidative Annulation of Thiocarbamates
R.Takishima, K. Ghosh, Y. Nishii, M. Miura
Synlett 2023 accepted [Link]

Isoselenazole Synthesis by Rh-Catalyzed Direct Annulation of Benzimidates with Sodium Selenite
Q.-F. Xu-Xu, Y. Nishii, M. Miura
Chemistry 2023, 5, 2068-2074. [Link]

Stimuli-Responsive Properties on a Bisbenzofuropyrazine Core: Mechanochromism and Concentration-Controlled Vapochromism
S. Nakamura, K. Okubo, Y. Nishii, K. Hirano, N. Tohnai, M. Miura
Chem. Eur. J. 2023, e202302605. [Link]

Rhodium-Catalyzed Isoquinoline Synthesis Using Vinyl Selenone as Oxidizing Acetylene Surrogate
A. Inami, Y. Nishii, K. Hirano, M. Miura
Org. Lett. 2023, 25, 3206-3209. [Link]

Preparation and Use of (γ,γ-Dioxyallyl)boronates
S. Nishino, Y. Nishii, K. Hirano
Synlett 2023, 34, 2205-2209. [Link]

One-Step Synthesis of Benzophosphole Derivatives from Arylalkynes by Phosphenium-Dication-Mediated Sequential C-P/C-C Bond Forming Reaction
K. Nishimura, S. Xu, Y. Nishii, K. Hirano
Org. Lett. 2023, 25, 1503-1508. [Link]

2022

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Synthesis of Diarylselenides through Rh-Catalyzed Direct Diarylation of Elemental Selenium with Benzamides
Q.-F. Xu-Xu, Y. Nishii, M. Miura
J. Org. Chem. 2022, 87, 16887-16894. [Link]

anti-Selective synthesis of β-boryl-α-amino acid derivatives by Cu-catalysed borylamination of α,β-unsaturated esters
S. Nishino, Y. Nishii, K. Hirano
Chem. Sci. 2022, 13, 14387-14394. [Link]

Ligand-Enabled Copper-Catalyzed Regio- and Stereoselective Allylboration of 1-Trifluoromethylalkenes
Y. Kojima, Y. Nishii, K. Hirano
Org. Lett. 2022, 24, 7450-7454. [Link]

Selective Synthesis of C4-Functionalized Benzofurans by Rhodium-Catalyzed Vinylene Transfer: Computational Study on the Cyclopentadienyl Ligand
J. Kitano, Y. Nishii, M. Miura
Org. Lett. 2022, 24, 5679-5683. [Link]

Effect of Halogens in Bis(haloaryloxyl)pyrazine Host Crystals on the Room Temperature Phosphorescence Properties of Bisbenzofuropyrazine Guest Luminophores
M. Tsuboi, S. Nakamura, Y. Nishii, N. Tohnai, M. Miura
Chem. Lett. 2022, 51, 819-822. [Link]

2021

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Synthesis of Benzoisoselenazolones via Rh(III)-Catalyzed Direct Annulative Selenation Using Elemental Selenium
Q.-F. Xu-Xu, Y. Nishii, Y. Uetake, H. Sakurai, M. Miura
Chem. Eur. J. 2021, 27, 17952-17959. [Link]

Sulfur-Directed C7-Selective Alkenylation of Indoles under Rhodium Catalysis
C. N. Kona, Y. Nishii, M. Miura
Org. Lett. 2021, 23, 6252-6256. [Link]

Rhodium-catalysed direct formylmethylation using vinylene carbonate and sequential dehydrogenative esterification
M. Kato, K. Ghosh, Y. Nishii, M. Miura
Chem. Commun. 2021, 57, 8280-8283. [Link]

Electrophilic Substitution of Asymmetrically Distorted Benzenes within Triptycene Derivatives
K. Ueno, Y. Nishii, M. Miura
Org. Lett. 2021, 23, 3552-3556. [Link]

Peri-Selective Direct Acylmethylation and Amidation of Naphthalene Derivatives Using Iridium and Rhodium Catalysts
C. N. Kona, R. Oku, Y. Nishii, M. Miura
Synthesis 2021, 53, 3126-3136. [Link]

Synthesis, Structure, and Chiroptical Properties of Indolo- and Pyridopyrrolo-Carbazole-Based C2-Symmetric Azahelicenes
T. Taniguchi, Y. Nishii, T. Mori, K. Nakayama, M. Miura
Chem. Eur. J. 2021, 27, 7356-7361. [Link]

Metal-Free Direct Trifluoromethylthiolation of Aromatic Compounds Using Triptycenyl Sulfide Catalyst
R. Kurose, Y. Nishii, M. Miura
Org. Lett. 2021, 23, 2380-2385. [Link]

Synthesis and Optical Properties of Axially Chiral Bibenzo[b]carbazole Derivatives
R. Takishima, Y. Nishii, M. Miura
Org. Lett. 2021, 23, 4, 1349-1354. [Link]

Synthesis of Isothiazoles and Isoselenazoles through Rhodium-Catalyzed Oxidative Annulation with Elemental Sulfur and Selenium
S. Moon, Y. Nishii, M. Miura
Org. Lett. 2021, 23, 1, 49-53. [Link]

2020

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Concise Synthesis of Isocoumarins through Rh-Catalyzed Direct Vinylene Annulation: Scope and Mechanistic Insight
G. Mihara, K. Ghosh, Y. Nishii, M. Miura
Org. Lett. 2020, 22, 5706-5711.[Link]

Thioether-Directed C4-Selective C-H Acylmethylation of Indoles Using α-Carbonyl Sulfoxonium Ylides
C. N. Kona, Y. Nishii, M. Miura
Org. Lett. 2020, 22, 4806-4811. [Link]

Room Temperature Phosphorescent Crystals Consisting of Cyclized Guests and Their Uncyclized Mother Host Molecules
S. Nakamura, M. Tsuboi, T. Taniguchi, Y. Nishii, N. Tohnai, M. Miura
Chem. Lett. 2020, 49, 921-924. [Link]

Oxidative C-H/C-H Annulation of Imidazopyridines and Indazoles through Rhodium-Catalyzed Vinylene Transfer
K. Ghosh, Y. Nishii, M. Miura
Org. Lett. 2020, 22, 3547-3550. [Link]

Copper-Catalyzed Site-Selective Direct Arylation of Triptycene
K. Ueno, Y. Nishii, M. Miura
Chem. Lett. 2020, 49, 689-692. [Link]

Synthesis and circularly polarized luminescence properties of BINOL-derived bisbenzofuro[2,3-b:3’,2’-e]pyridines (BBZFPys)
R. Takishima, Y. Nishii, T. hinoue, Y. Imai, M. Miura
Beilstein J. Org. Chem. 2020, 16, 325-336. [Link]

Synthesis of Benzo[b]thiophenes through Rhodium‐Catalyzed Three‐Component Reaction using Elemental Sulfur
S. Moon, M. Kato, Y. Nishii, M. Miura
Adv. Synth. Catal. 2020, 362, 1669-1673. [Link]

Rhodium-Catalyzed Annulative Coupling of Isothiazoles with Alkynes through N-S Bond Cleavage
G. Mihara, T. Noguchi, Y. Nishii, Y. Hayashi, S. Kawauchi, M. Miura
Org. Lett. 2020, 22, 661-665 [Link]

Triptycenyl Sulfide: A Practical and Active Catalyst for Electrophilic Aromatic Halogenation using N-Halosuccinimides
Y. Nishii, M. Ikeda, Y. Hayashi, S. Kawauchi, M. Miura
J. Am. Chem. Soc 2020, 142, 1621-1629. [Link]

Synthesis and Properties of Tri-tert-Butylated Trioxa and Trithia Analogues of Truxene
S. Nakamura, M. Okamoto, N. Tohnai, K. Nakayama, Y. Nishii, M. Miura
Bull. Chem. Soc. Jpn. 2020, 93, 99-108. [Link]

before 2020

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Rhodium-Catalyzed Annulative Coupling Using Vinylene Carbonate as Oxidizing Acetylene Surrogate
K. Ghosh, Y. Nishii, M. Miura
ACS Catal. 2019, 9, 11455-11460. [Link]

Composite Tetraheteroarylenes and Related Higher Cyclic Oligomers of Heteroarenes Produced by Palladium-Catalyzed Direct Coupling
K. Fukuzumi, Y. Nishii, M. Miura
Bull. Chem. Soc. Jpn. 2019, 92, 2030-2037. [Link]

Construction of Nitrogen-Containing Policyclic Aromatic Compounds by Intramolecular Oxidative C-H/C-H Coupling of Bis(9H-Carbazol-9-yl)benzenes and Their Properties
T. Taniguchi, Y. Itai, Y. Nishii, N. Tohnai, M. Miura
Chem. Lett. 2019, 48, 1160-1163. [Link]

Iridium‐Catalyzed Direct C4‐ and C7‐Selective Alkynylation of Indoles Using Sulfur‐Directing Groups
C. Kona, Y. Nishii, M. Miura
Angew. Chem. Int. Ed. 2019, 58, 9856-9860. [Link]

Nondirected C-H Alkenylation of Arenes with Alkenes under Rhodium Catalysis
K. Ghosh, G. Mihara, Y. Nishii, M. Miura
Chem. Lett. 2019, 48, 148-151. [Link]

Thioether-Directed Peri-Selective C-H Arylation under Rhodium Catalysis: Synthesis of Arene-Fused Thioxanthenes
S. Moon, Y. Nishii, M. Miura
Org. Lett. 2019, 21, 233-236. [Link]

Rhodium-Catalyzed Cascade Annulative Coupling of 3,5-Diarylisoxazoles with Alkynes
T. Noguchi, Y. Nishii, M. Miura
Synthesis 2019, 51, 258-270. [Link]
Highlighted in Synfacts 2019, 15(05), 0489. [Link]

Effect of Substitution Pattern of tert‐Butyl Group in a Bisbenzofuropyrazine Core π‐System on Optical Property: Unique Mechanochromic Fluorescence Behavior
S. Nakamura, N. Tohnai, Y. Nishii, T. Hinoue, M. Miura
ChemPhotoChem 2019, 3, 46-53. [Link]

Syntheses of Diverse Donor-Substituted Bisbenzofuro[2,3-b:3',2'-e]pyridines (BBZFPys) via Pd Catalysis, and Their Photophysical Properties
Y. Itai, Y. Nishii, P. Stachelek, P. Data, Y. Takeda, S. Minakata, M. Miura
J. Org. Chem. 2018, 83, 10289-10302.[Link]

Thioether-Directed Selective C4 C-H Alkenylation of Indoles under Rhodium Catalysis
C. Kona, Y. Nishii, M. Miura
Org. Lett. 2018, 20, 4898-4901.[Link]

Rhodium‐Catalyzed peri‐Selective Direct Alkenylation of 1‐(Methylthio)naphthalene
M. Shigeno, Y. Nishii, T. Satoh, M. Miura
Asian J. Org. Chem. 2018, 7, 1334-1337. [Link]

Synthesis, crystal structure and reactivity of η2-thiophyne Ni complexes
M. Terada, Y. Nishii, M. Miura
Chem. Commun. 2018, 54, 2918-2921.[Link]

Palladium-Catalyzed Synthesis of Heteroarene-Fused Cyclooctatetraenes through Dehydrogenative Cyclodimerization
K. Fukuzumi, Y, Nishii, M. Miura
Angew. Chem. Int. Ed. 2017, 56, 12746-12750. [Link]

Rhodium-catalyzed Sythesis of 1-Arylisoquinoline Derivatives through Annulative Coupling of 3-Aryl-1,2-benzisoxazoles and Alkynes
T. Noguchi, Y. Nishii, M. Miura
Chem. Lett. 2017, 46, 1512-1514. [Link]

Rhodium-catalyzed Sythesis of 1-(Acylamino)isoquinolines through Direct Annulative Coupling of 3-Aryl-1,2,4-oxadiazoles with Alkynes
Y. Nishii, A.-K. Bachon, S. Moon, C. Bolm, M. Miura
Chem. Lett. 2017, 46, 1347-1349. [Link]

Palladium-Catalyzed Direct C2-Arylation of Benzo[b]thiophenes with Electron-Rich Aryl Halides: Facile Access to Thienoacene Derivatives
F. Ichioka, Y. Itai, Y. Nishii, M. Miura
Synlett 2017, 28, 2812-2816. [Link]

Construction of Bisbenzofuro[2,3-b:3',2'-e]pyridines by Palladium-Catalyzed Double Intramolecular Oxidative C-H/C-H Coupling
H. Kaida, T. Goya, Y, Nishii, K. Hirano, T. Satoh, M. Miura
Org. Lett. 2017, 19, 1236-1239. [Link]

Zinc-catalyzed Esterification of N-β-Hydroxyethylamides; Removal of Directing Groups under Mild Conditions
Y. Nishii, T. Hirai, S. Fernandez, P. Knochel, K. Mashima
Eur. J. Org. Chem. 2017, 2017, 5010-5014. [Link]

Synthesis of Benzo-bis- and Benzo-tris-benzofurans by Palladium-Catalyzed Multiple Intramolecular C-H/C-H Coupling
H. Kaida, T. Satoh, Y, Nishii, K. Hirano, M. Miura
Chem. Lett. 2016, 45, 1069-1071. [Link]

Rhodium-Catalyzed Oxidative Annulation of (2-Arylphenyl)boronic Acids with Alkynes: Selective Synthesis of Phenanthrene Derivatives
T. Nagata, T. Satoh, Y, Nishii, M. Miura
Synlett. 2016, 11, 1707-1710. [Link]

Synthesis of Benzo[c]thiophenes by Rhodium(III)-Catalyzed Dehydrogenative Annulation
K. Fukuzumi, Y. Unoh, Y. Nishii, T. Satoh, K. Hirano, M. Miura
J. Org. Chem. 2016, 81, 2474-2481. [Link]

Manganese(II) Catalyzed Esterification of N-β-Hydroxyethylamides
Y. Nishii, S. Akiyama, Y. Kita, K. Mashima
Synlett 2015, 26, 1831-1834. [Link]

Combined Catalytic System of Scandium Triflate and Boronic Ester for Amide Bond Cleavage
Y. Kita, Y. Nishii, A. Onoue, K. Mashima
Adv. Synth. Catal. 2013, 355, 3391-3395. [Link]

Zinc-Catalyzed Amide Cleavage and Esterification of b-Hydroxyethylamides
Y. Kita, Y. Nishii, T. Higuchi, K. Mashima
Angew. Chem. Int. Ed. 2012, 51, 5723-5726. [Link]

Review & Account

Construction of multi-ring molecules through direct C-H bond transformation
Y. Nishii, K.Hirano, T. Satoh, M. Miura
Bull. Chem. Soc. Japan 2024, 97. [Link]

Construction of Benzo-Fused Polycyclic Heteroaromatic Compounds through Palladium-Catalyzed Intramolecular C-H/C-H Biaryl Coupling
Y. Nishii, M. Miura
Catalysts 2023, 13, 12. [Link]

Utilization of sulfur function in directed catalytic C-H transformation: Site-selective substitution on indole and naphthalene skeletons
Y. Nishii, M. Miura
Phosphorus Sulfur Silicon Relat. Elem. 2022, accepted. [Link]

Cp*M-Catalyzed Direct Annulation with Terminal Alkynes and Their Surrogates for the Construction of Multi-Ring Systems
Y. Nishii, M. Miura
ACS catal. 2020, 10, 9747-9757. [Link]

Catalytic Cleavage of Amide C-N Bond: Scandium, Manganese, and Zinc Catalysts for Esterification of Amides
K. Mashima, Y. Nishii, H.Nagae
Chem. Rec. 2020, 20, 332-343. [Link]

Patent

特願2023-081147 カルボラン化合物及びそれを用いたハロゲン化芳香族化合物の製造方法 西井祐二