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島根大学大学院自然科学研究科 物質化学コース

Department of Chemistry

Graduate School of Natural Science and Technology
Shimane University

研究業績_飯田拡基PUBLICATIONS


2021



Encapsulation of Aromatic Guests in Bisporphyrin Cavity of a Double-Stranded Spiroborate Helicate: Thermodynamic and Kinetic Studies and Encapsulation Mechanism
N. Ousaka, S. Yamamoto, H. Iida, T. Iwata , S. Ito , R. Souza, Y. Hijikata, S. Irle, E. Yashima
J. Org. Chem., 2021, 86, 10501-10516



Green Aerobic Oxidation of Thiols to Disulfides by Flavin–Iodine Coupled Organocatalysis
M. Oka, R. Kozako, H. Iida
Synlett, 2021, 32, 1227-1230










Aerobic Oxidative C-H Azolation of Indoles and One-Pot Synthesis of Azolyl Thioindoles by Flavin–Iodine-Coupled Organocatalysis
K. Tanimoto, H. Okai, M. Oka, R. Ohkado, H. Iida
Org. Lett. 2021, 23, 2084-2088










2020


Phototropin-Inspired Chemoselective Synthesis of Unsymmetrical Disulfides: Aerobic Oxidative Heterocoupling of Thiols using Flavin Photocatalysis
M. Oka, D. Katsube, T. Tsuji, H. Iida
Org. Lett. 2020, 22, 9244-9248




Multi-Component Synthesis of Imidazo[1,2-a]pyridines: Aerobic Oxidative Formation of C-N and C-S Bonds by Flavin–Iodine-Coupled Organocatalysis
H. Okai, K. Tanimoto, R. Ohkado, H. Iida
Org. Lett., 2020, 22, 8002-8006




Non-Covalently Immobilized Chiral Imidazolidinone on Sulfated-Chitin: Reusable Heterogeneous Organocatalysts for Asymmetric Diels-Alder Reaction
M. Watanabe, T. Sakai, M. Oka, Y. Makinose, H. Miyazaki, H. Iida
Adv. Synth. Catal., 2020, 362, 255-260









2019


Aerobic Oxidative Sulfenylation of Pyrazolones and Pyrazoles Catalyzed by Metal-Free Flavin–Iodine Catalysis
K. Tanimoto, R. Ohkado, H. Iida
J. Org. Chem., 2019, 84, 14980-14986.




Fluorescent molecular spring that visualizes the extension and contraction motions of a double-stranded helicate bearing terminal pyrene units triggered by release and binding of alkali metal ions
D. Taura, K. Shimizu, C. Yokota, R. Ikeda, Y. Suzuki, H. Iida, N. Ousaka, E. Yashima
Chem. Commun., 2019, 55, 12084-12087.



The helix-inversion mechanism in double-stranded helical oligomers bridged by rotary cyclic boronate esters
T. Hayashi, K. H. Lee, H. Iida, E. Yashima, S. Irle, Y. Hijikata
J. Comput. Chem., 2019, 40, 2036-2042.



Water-mediated deracemization of a bisporphyrin helicate assisted by diastereoselective encapsulation of chiral guests
N. Ousaka, S. Yamamoto, H. Iida, T. Iwata, S. Ito, Y. Hijikata, S. Irle, E. Yashima
Nature Commun., 2019, 10, 1457.



Flavinium and Alkali Metal Assembly on Sulfated Chitin: A Heterogeneous Supramolecular Catalyst for H2O2-Mediated Oxidation
T. Sakai, M. Watanabe, R. Ohkado, Y. Arakawa, Y. Imada, H. Iida
ChemSusChem, 2019, 12, 1640-1645.

2018


Spiroborate-Based Double-Stranded Helicates: Meso-to-Racemo Isomerization and Ion-Triggered Spring-Like Motion of the Racemo-Helicate
N. Ousaka, K. Shimizu, Y. Suzuki, T. Iwata, M. Itakura, D. Taura, H. Iida, Y. Furusho, T. Mori, E. Yashima
J. Am. Chem. Soc., 2018, 140, 17027-17039.




Tandem Flavin-Iodine-Catalyzed Aerobic Oxidative Sulfenylation of Imidazo[1,2-a]Pyridines with Thiols
H. Iida, R. Demizu, R. Ohkado
J. Org. Chem., 2018, 83, 12291-12296.









Comparison of Riboflavin-Derived Flavinium Salts Applied to Catalytic H2O2 Oxidations
T. Sakai, T. Kumoi, T. Ishikawa, T, Nitta, H. Iida
Org. Biomol. Chem., 2018, 16, 3999-4007.












Flavin–Iodine Coupled Organocatalysis for Aerobic Oxidative Direct Sulfenylation of Indoles with Thiols under Mild Conditions
R. Ohkado, T. Ishikawa, H. Iida
Green Chem., 2018, 20, 984-988.











2017


Coupled Flavin-Iodine Redox Organocatalysts: Aerobic Oxidative Transformation from N-Tosylhydrazones to 1,2,3-Thiadiazoles
T. Ishikawa, M. Kimura, T. Kumoi, H. Iida
ACS Catal., 2017, 7, 4986-4989. (Selected as a Front Cover)

















Double-Stranded Helical Oligomers Covalently-Bridged by Rotary Cyclic Boronate Esters
H. Iida, K. Ohmura, R. Noda, S. Iwahana, H. Katagiri, N. Ousaka, T. Hayashi, Y. Hijikata, S. Irle, E. Yashima
Chem. Asian J.
, 2017, 12, 927-935
. (Selected as a Front Cover)
















2016


Anion effect of 5-ethylisoalloxazinium salts on flavin-catalyzed oxidations with H2O2
H. Iida, T. Ishikawa, K. Nomura, S.-I. Murahashi
Tetrahedron Lett.
, 2016, 47, 4488-4491.













Allosteric Regulation of Unidirectional Spring-like Motion of Double-Stranded Helicates
Y. Suzuki, T. Nakamura, H. Iida, N. Ousaka, E. Yashima
J. Am. Chem. Soc., 2016, 138, 4852-4859.


2015


Helical Poly(phenylacetylene)s Bearing Chiral and Achiral Imidazolidinone-Based Pendants that Catalyze Asymmetric Reaction due to Catalytically Active Achiral Pendants Assisted by Macromolecular Helicity
L. M. S. Takata, H. Iida, K. Shimomura, K. Hayashi, A. A. dos Santos, E. Yashima
Macromol. Rapid Commun., 2015, 36, 2047-2054.





Chirality- and sequence-selective successive self-sorting via specific homo- and complementary-duplex formations
W. Makiguchi, J. Tanabe, H. Yamada, H. Iida, D. Taura, N. Ousaka, E. Yashima
Nature Commun., 2015, 6:7236 doi: 10.1038/ncomms8236



Enantioseparation on Riboflavin Derivatives Chemically Bonded to Silica Gel as Chiral Stationary Phases for HPLC
D. Kumano, S. Iwahana, H. Iida, C. Shen, J. Crassous, E. Yashima
Chirality, 2015, 27, 507-517.



Homo-Double Helix Formation of an Optically Active Conjugated Polymer Bearing Carboxy Groups and Amplification of The Helicity upon Complexation with Achiral and Chiral Amines
W. Makiguchi, S. Kobayashi, K. Furukawa, H. Iida, Y. Furusho, E. Yashima
J. Polym. Sci., Part A: Polym. Chem., 2015, 53, 990-999.


2014


Flavin-Catalyzed Aerobic Oxidation of Sulfides and Thiols with Formic Acid/Triethylamine
S.-I. Murahashi, D. Zhang, H. Iida, T. Miyawaki, M. Uenaka, K. Murano, K. Meguro
Chem. Commun., 2014, 50, 10295-10298.



Synthesis and Chiral Recognition Ability of Helical Polyacetylenes Bearing Helicene Pendants
E. Anger, H. Iida, T. Yamaguchi, K. Hayashi, D. Kumano, J. Crassous, N. Vanthuyne, C. Roussel, E. Yashima
Polym. Chem., 2014, 5, 4909-4914. (Selected as a Back Cover)















Riboflavin-Based Fluorogenic Sensor for Chemo- and Enantioselective Detection of Amine Vapors
H. Iida, M. Miki, S. Iwahana, E. Yashima
Chem. Eur. J., 2014, 20, 4257-4262.
















Absolute Stereochemistry of a 4a-Hydroxyriboflavin Analogue of the Key Intermediate of the FAD-Monooxygenase Cycle
S. Iwahana, H. Iida, E. Yashima, G. Pescitelli, L. D. Bari, A. G. Petrovic, N. Berova
Chem. Eur. J., 2014, 20, 4386-4395.


2013


Photoswitchable Organocatalysis in Acylation of Alcohol Using Dithienylethene-Linked Azoles
H. Iida, N. Umebayashi, E. Yashima
Tetrahedron, 2013, 69, 11064-11069.














Guest-Induced Unidirectional Dual Rotary and Twisting Motions of a Spiroborate-Based Double-Stranded Helicate Containing a Bisporphyrin Unit
S. Yamamoto, H. Iida and E. Yashima
Angew. Chem., Int. Ed., 2013, 52, 6849-6853.



Synthesis and Bifunctional Asymmetric Organocatalysis of Helical Poly(phenylacetylene)s Bearing Cinchona Alkaloid Pendants via a Sulfonamide Linkage
H. Iida, Z. Tang and E. Yashima
J. Polym. Sci., Part A: Polym. Chem.
, 2013, 51, 2869-2879.




Electrical Switching Behavior of a [60]Fullerene-Based Molecular Wire Encapsulated in a Syndiotactic Poly(methyl methacrylate) Helical Cavity
S. Qi, H. Iida, L. Liu, S. Irle, W. Hu and E. Yashima
Angew. Chem., Int. Ed., 2013, 52, 1049-1053. (Selected as an Inside Cover)














2012


Remarkable Enhancement of the Enantioselectivity of an Organocatalyzed Asymmetric Henry Reaction Assisted by Helical Poly(phenylacetylene)s Bearing Cinchona Alkaloid Pendants via an Amide Linkage
Z. Tang, H. Iida, H.-Y. Hu and E. Yashima
ACS Macro Lett., 2012, 1, 261-265.













Enantioseparation on Helical Poly(phenylacetylene)s Bearing Cinchona Alkaloid Pendants as Chiral Stationary Phases for HPLC
Y. Naito, Z. Tang, H. Iida, T. Miyabe and E. Yashima
Chem. Lett., 2012, 41, 809-811.



Enantioseparation on Poly(phenyl isocyanide)s with Macromolecular Helicity Memory as Chiral Stationary Phases for HPLC
T. Miyabe, H. Iida and E. Yashima
Chem. Sci., 2012, 3, 863-867.



Main-Chain Optically Active Riboflavin Polymer for Asymmetric Catalysis and Its Vapochromic Behavior
H. Iida, S. Iwahana, T. Mizoguchi and E. Yashima
J. Am. Chem. Soc., 2012, 134, 15103-15113.














2011


Synthesis and Visualization of a Core Cross-Linked Star Polymer Carrying Optically Active Rigid-Rod Helical Polyisocyanide Arms and Its Chiral Recognition Ability
T. Miyabe, H. Iida, M. Banno, T. Yamaguchi and E. Yashima
Macromolecules, 2011, 44, 8687-8692.



Synthesis of Helical Poly(phenylacetylene)s Bearing Cinchona Alkaloid Pendants and Their Application to Asymmetric Organocatalysis
G. M. Miyake, H. Iida, H.-Y. Hu, Z. Tang, E. Y. X. Chen and E. Yashima
J. Polym. Sci., Part A: Polym. Chem.
, 2011, 49, 5192-5198.




Chiral Information Harvesting in Dendritic Metallopeptides
N. Ousaka, Y. Takeyama, H. Iida and E. Yashima
Nature Chem., 2011, 3, 856-861.



Separation of Enantiomers on Diastereomeric Right- and Left-Handed Helical Poly(phenyl isocyanide)s Bearing L-Alanine Pendants Immobilized on Silica Gel by HPLC
K. Tamura, T. Miyabe, H. Iida and E. Yashima
Polym. Chem., 2011, 2, 91-98.
Selected as a Front Cover



Helicity Induction and Memory of Syndiotactic Poly(methyl methacrylate) Assisted by Optically Active Additives and Solvents and Chiral Amplification of Helicity
A. Kitaura, H. Iida, T. Kawauchi and E. Yashima
Chem. Lett., 2011, 40, 28-30.



Oxidative Esterification, Thioesterification, and Amidation of Aldehydes by a Two-Component Organocatalyst System Using a Chiral N-Heterocyclic Carbene and Redox-Active Riboflavin
S. Iwahana, H. Iida and E. Yashima
Chem. Eur. J., 2011, 17, 8009-8013.














Aerobic Reduction of Olefins by In Situ Generation of Diimide with Synthetic Flavin Catalysts
Y. Imada, H. Iida, T. Kitagawa and T. Naota
Chem. Eur. J., 2011, 17, 5908-5920.




Before 2011

Separation of C70 over C60 and Selective Extraction and Resolution of Higher Fullerenes by Syndiotactic Helical Poly(methyl methacrylate)
T. Kawauchi, A. Kitaura, M. Kawauchi, T. Takeichi, J. Kumaki, H. Iida and E. Yashima
J. Am. Chem. Soc., 2010, 132, 12191-12193.



Neutral Flavins: Green and Robust Organocatalysts for Aerobic Hydrogenation of Olefins
Y. Imada, T. Kitagawa, T. Ohno, H. Iida and T. Naota
Org. Lett., 2010, 12, 32-35.



Double-Stranded Supramolecular Assembly through Salt Bridge Formation between Rigid and Flexible Amidine and Carboxylic Acid Strands
H. Iida, M. Shimoyama, Y. Furusho and E. Yashima
J. Org. Chem., 2010, 75, 417-423.



Redox-Triggered Switching of Helical Chirality of Poly(phenylacetylene)s Bearing Riboflavin Pendants
H. Iida, T. Mizoguchi, S.-D. Oh and E. Yashima
Polym. Chem., 2010, 1, 841-848.



Synthesis of Functional Poly(phenyl isocyanide)s with Macromolecular Helicity Memory and Their Use as Asymmetric Organocatalysts
T. Miyabe, Y. Hase, H. Iida, K. Maeda and E. Yashima
Chirality, 2009, 21, 44-50.



Helix Formation of Poly(phenylacetylene)s Bearing Azide Groups through Click Polymer Reaction with Optically Active Acetylenes
K. Itomi, S. Kobayashi, K. Morino, H. Iida and E. Yashima
Polym. J., 2009, 41, 108-109.



Mechanism of Helix Induction in Poly(4-carboxyphenyl isocyanide) with Chiral Amines and Memory of the Macromolecular Helicity and Its Helical Structures
Y. Hase, K. Nagai, H. Iida, K. Maeda, N. Ochi, K. Sawabe, K. Sakajiri, K. Okoshi and E. Yashima
J. Am. Chem. Soc., 2009, 131, 10719-10732.



Polymerization of an Optically Active Phenylacetylene Derivative Bearing an Azide Residue by Click Reaction and with a Rhodium Catalyst
S. Kobayashi, K. Itomi, K. Morino, H. Iida and E. Yashima
Chem. Commun., 2008, 3019-3021.



Diastereo- and Enantioselective Hydrogenative Aldol Coupling of Vinyl Ketones: Design of Effective Monodentate TADDOL-Like Phosphonite Ligands
C. Bee, S. B. Han, A. Hassan, H. Iida and M. J. Krische
J. Am. Chem. Soc., 2008, 130, 2746 - 2747.



Flavin-Catalyzed Oxidation of Amines and Sulfides with Molecular Oxygen: Biomimetic Green Oxidation
Y. Imada, H. Iida, S. Ono, Y. Masui and S.-I. Murahashi
Chem. Asian. J., 2006, 1, 136-147.



Flavin-Catalyzed Generation of Diimide: An Environmentally Friendly Method for the Aerobic Hydrogenation of Olefins
Y. Imada, H. Iida and T. Naota
J. Am. Chem. Soc., 2005, 127, 14544 - 14545.



An Aerobic, Organocatalytic, and Chemoselective Method for Baeyer-Villiger Oxidation
Y. Imada, H. Iida, S.-I. Murahashi and T. Naota
Angew. Chem., Int. Ed., 2005, 44, 1704-1706.



Flavin Catalyzed Oxidations of Sulfides and Amines with Molecular Oxygen
Y. Imada, H. Iida, S. Ono and S.-I. Murahashi
J. Am. Chem. Soc., 2003, 125, 2868-2869.




Reviews


Biomimetic flavin-catalysed reactions for organic synthesis
H. Iida, Y. Imada, S.-I. Murahashi
Org. Biomol. Chem., 2015, 13, 7599-7613.










Enantiomeric Differentiation by Synthetic Helical Polymers
E. Yashima, H. Iida and Y. Okamoto
Top. Curr. Chem., 2013, 340, 41-72.



Helical Polymers: Synthesis, Structures, and Functions
E. Yashima, K. Maeda, H. Iida, Y. Furusho and K. Nagai
Chem. Rev., 2009, 109, 6102-6211.



Catalytic Reductive Coupling of Alkenes and Alkynes to Carbonyl Compounds and Imines Mediated by Hydrogen
H. Iida and M. J. Krische
Top. Curr. Chem., 2007, 411, 77-104.




その他

解説

らせん高分子の合成とキラル識別材料への応用: Synthesis of Helical Polymers and Their Application to Chiral Materials for Chiral Recognition
飯田拡基, 八島栄次
化学工業, 2012, 63, 54-62.



機能性キラル材料としてのらせん高分子"
飯田拡基, 八島栄次
未来材料, 2011, 5, 20-28.



らせん構造制御を基盤とする機能性高分子の創製と応用
八島栄次, 飯田拡基
科学と工業, 2009, 83, 10-17.


著書

Organocatalytic Monooxygenations
H. Iida, Y. Imada
In Flavin-Based Catalysis (Eds.: R. Cibulka, M. W. Fraaije), Wiley-VCH, Weinheim, 2021, pp. 125-144.



Flavin-Based Supramolecular and Coupled Catalytic Systems
H. Iida, Y. Imada
In Flavin-Based Catalysis (Eds.: R. Cibulka, M. W. Fraaije), Wiley-VCH, Weinheim, 2021, pp. 145-168.



Synthesis and Application of Helical Polymers with Macromolecular Helicity Memory
H. Iida and E. Yashima
In Polymeric Chiral Catalyst Design and Chiral Polymer Synthesis (Ed.: S. Itsuno), Wiley, 2011, pp. 201-222.


特許

“光学異性体用分離剤”, 特願2012-108689, 2012年5月10日
八島栄次, 飯田拡基, タンチェンリン, 内藤裕樹




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