MIURA Masahiro
Division of Applied Chemistry, Graduate School of Engineering
Department of Applied Chemistry, Faculty of Engineering, Osaka University, Suita, Osaka 565-0871,Japan
Organization
- 1998.04.01 - 2005.03.31, Graduate School of Engineering, Associate Professor, full time
- 2005.04.01 - , Division of Applied Chemistry, Graduate School of Engineering, Professor, full time
Education
| Osaka University Faculty of Engineering Graduated 78' | ||
| Osaka University Graduate School, Division of Engineering Completed 83' |
Research topics
- Development of New, Efficient Catalytic Reactions for Organic Synthesis
Organic chemistry - Design and Synthesis of Functionalized Aromatic Compounds
Organic and hybrid materials
We are performing basic and applied research on various organic molecules including small ones such as carbon monoxides and macro-ones derived from petroleum and coal to develop their new reactivities. The central goals of our studies are to develop (1) new methods and efficient strategies for the synthesis of organic fine chemicals including pharmaceutical intermediates and p-conjugated functional materials and (2) high-performance catalysts enabling effective functionalization of organic molecules.
[Recent Publications]
Rhodium-catalyzed oxidative coupling of aromatic imines with internal alkynes via regioselective C-H bond cleavage, T. Fukutani, N. Umeda, K. Hirano, T. Satoh, M. Miura, Chem. Commun. 2009, in press.
Nickel-Catalyzed C-H Alkenylation and Alkylation of 1,3,4-Oxadiazoles with Alkynes and Styrenes, T. Mukai, K. Hirano, T. Satoh, M. Miura, J. Org. Chem. 2009, in press.
Synthesis of Functionalized α-Pyrone and Butenolide Derivatives by Rhodium-Catalyzed Oxidative Coupling of Substituted Acrylic Acids with Alkynes and Alkenes, S. Mochida, K. Hirano, T. Satoh, M. Miura, J. Org. Chem. 2009, in press.
Copper-Mediated Direct Arylation of 1,3,4-Oxadiazoles and 1,2,4-Triazoles with Aryl Iodides, T. Kawano, T. Yoshizumi, K. Hirano, T. Satoh, M. Miura, Org. Lett. 2009, 11, 3072-3075.
Synthesis of Condensed Heteroaromatic Compounds by Palladium-Catalyzed Oxidative Coupling of Heteroarene Carboxylic Acids with Alkynes, M. Yamashita, K. Hirano, T. Satoh, M. Miura, Org. Lett. 2009, 11, 2337-2340.
Nickel- and Rhodium-Catalyzed Addition of Terminal Silylacetylenes to Propargyl Amines Catalyst-Dependent Complementary Regioselectivity, N. Matsuyama, K. Hirano, T. Satoh, M. Miura, J. Org. Chem. 2009, 74, 3576-3578.
Waste-free Synthesis of Condensed Heterocyclic Compounds by Rhodium-catalyzed Oxidative Coupling of Substituted Arene or Heteroarene Carboxylic Acids with Alkynes, M. Shimizu, K. Hirano, T. Satoh, M. Miura, J. Org. Chem. 2009, 74, 3478-3483.
Nickel-catalyzed Direct Arylation of Azoles with Aryl Bromides, H. Hachiya, K. Hirano, T. Satoh, M. Miura, Org. Lett. 2009, 11, 1737-1740.
Fluorescent Diarylindoles by Palladium-Catalyzed Direct and Decarbonylative Arylations of Carboxyindoles, M. Miyasaka, A. Fukushima, T. Satoh, K. Hirano, M. Miura, Chem, Eur, J. 2009, 15, 3674-3677
Rhodium-Catalyzed and Coordination-Assisted Regioselective Alkenylation of Aromatic C-H Bonds with Terminal Silylacetylenes, T. Katagiri, T. Mukai, T.Satoh, K. Hirano, M. Miura, Chem. Lett. 2009, 38, 118-119.
Ligand-Controlled Cross-Dimerization and -Trimerization of Alkynes under Nickel Catalysts, N. Matsuyama, H. Tsurugi, T. Satoh, M. Miura, Adv. Synth. Catal. 2008, 350, 2274-2278.
Rhodium-Catalyzed (E)-Selective Cross-Dimerization of Terminal Alkynes, T. Katagiri, H. Tsurugi, T. Satoh, M. Miura, Chem. Commun.2008, 29, 3405-3407.
Rhodium-Catalyzed Regioselective Arylation of Phenylazoles and Related Compounds with Arylboron Reagents via C-H Bond Cleavage, S. Miyamura, T. Satoh, H. Tsurugi, M. Miura, J. Organomet. Chem. 2008, 693, 2438-2442.
Rhodium-Catalyzed Anti Selective Cross-Addition of Bis(trimethylsilyl)acetylenes to Diarylacetylenes via Carbon-Silicon Bond Cleavage, A. Horita, T. Satoh, H. Tsurugi, M. Miura, Org. Lett. 2008,10, 1751-1754.
Fluorescent Naphthyl- and Anthrylazoles from the Catalytic Coupling of Phenylazoles with Internal Alkynes through the Cleavage of Multiple C-H Bonds, N. Umeda, T. Satoh, H. Tsurugi, M. Miura, Angew. Chem. Int. Ed. 2008, 47, 4019-4022.
Rhodium-Catalyzed Oxidative Coupling between Salicylaldehydes and Internal Alkynes with C-H Bond Cleavage to Produce 2,3-Disubstituted Chromones, M. Shimizu, T. Satoh, H. Tsurugi, M. Miura, Chem. Asian J. 2008, 3, 881-886.
Palladium-Catalyzed Perarylation of 3-Thiophene- and 3-Furancarboxylic Acids Accompanied by C-H Bond Cleavage and Decarboxylation, M. Nakano, T. Satoh, H. Tsurugi, M. Miura, Org. Lett. 2008, 10, 1851-1854.
Regioselective C-H Functionalization Directed by a Removable Carboxyl Group : Palladium-Catalyzed Vinylation at the Unusual Position of Indole and Related Heteroaromatic Rings, A. Maehara, H. Tsurugi, T. Satoh, M. Miura, Org. Lett. 2008, 10, 1159-1162.
Copper-mediated direct arylation of benzoazoles with aryl iodides, T. Yoshizumi, H. Tsurugi, T. Satoh, M. Miura, Tetrahedron Lett., 2008,49, 1598-1600.
Palladium/Phosphite or Phosphate Catalyzed Oxidative Coupling of Arylboronic Acids with Alkynes to Produce 1,4-Diaryl-1,3-Butadienes, H. Horiguchi, H. Tsurugi, T. Satoh, M. Miura, Adv. Synth. Catal., 2008, 49, 509-514.
Palladium/Phosphite-Catalyzed 1,4-Addition of Arylboronic Acids to Acrylic Acid Derivatives, H. Horiguchi, H. Tsurugi, T. Satoh, M. Miura, J. Org. Chem., 2008, 73, 1590-1592.
Palladium-Catalyzed Direct Oxidative Vinylation of Thiophenes and Furans under Weakly Basic Conditions, A. Maehara, T. Satoh, M. Miura, Tetrahedron, 2008, 64, 5982-5986.
Rhodium- and Iridium-Catalyzed Oxidative Coupling of Benzoic Acids with Alkynes and Alkenes, T. Satoh, K. Ueura, M. Miura, Pure Appl. Chem. 2008, 80, 1127-1134.
Continuous Hydrogen Evolution from Cyclohexanes over Platinum Catalysts Supported on Activated Carbon Fibers, P. D. Tien, T. Satoh, M. Miura, M. Nomura, Fuel Process. Technol., 2008, 89, 415-418.
Rhodium-Catalyzed Oxidative Coupling of Triarylmethanols with Internal Alkynes via Successive C-H and C-C Bond Cleavages, T. Uto, M. Shimizu, K. Ueura, H. Tsurugi, T. Satoh, M. Miura, J. Org. Chem., 2008, 73, 298-300.
Synthesis of Alkylated Benzo[2,1-b:3,4-b']dithiophenes by Annulative Coupling and Their Direct Arylation under Palladium Catalysis, H. Watanabe, J. Kumagai, H. Tsurugi, T. Satoh, M. Miura, Chem. Lett., 2007, 36, 1336-1337.
Catalytic Arylation and Vinylation Reactions Directed by Anionic Oxygen Functions via Cleavage of C-H and C-C Bonds, T. Satoh, M. Miura, Top. Organomet. Chem., 2008, 24, 61-84.
Palladium-Catalyzed Intermolecular Three-Component Coupling of Organic Halides with Alkynes and Alkenes: Efficient Synthesis of Oligoene Compounds, K. Shibata, T. Satoh, M. Miura, Adv. Synth. Catal., 2007, 349, 2317-2325.
Rhodium- and Iridium-Catalyzed Oxidative Coupling of Benzoic Acids with Alkynes via Regioselective C-H Bond Cleavage, K. Ueura, T. Satoh, M. Miura, J. Org. Chem., 2007, 72, 5362-5367.
Rhodium-Catalyzed Cross-Coupling of Internal Alkynes with a Terminal Silylacetylene, T. Katagiri, H. Tsurugi, A. Funayama, T. Satoh, M. Miura, Chem. Lett., 2007, 36, 830-831.
Regio- and Stereoselective Cross-Coupling of tert-Propargyl Alchohols with Bis(trimethylsilyl)acetylene and Its Utilization in Constructing a Fluorescent Donor-Acceptor Syetem, A. Horita, H. Tsurugi, A. Funayama, T. Satoh, M. Miura, Org. Lett., 2007, 9, 2231-2233.
An Efficient Waste-Free Oxidative Coupling via Regioselective C-H Bond Cleavage: Rh/Cu-Catalyzed Reaction of Benzoic Acids with Alkynes and Acrylates under Air, K. Ueura, T. Satoh, M. Miura, Org. Lett., 2007, 9, 1407-1409.
Rhodium-Catalyzed Diarylation of Oxalates Using Arylboron Compounds, S. Miyamura, T. Satoh, M. Miura, J. Org. Chem., 2007, 72, 2255-2257.
Catalytic Direct Arylation of Heteroaromatic Compounds, T. Satoh, M. Miura, Chem. Lett., 2007, 36, 200-205.
Miura-Lab tour, click here!!!
Synthesis of Carbazoles by Copper-Catalyzed Intramolecular C-H/N-H Coupling
K. Takamatsu, K. Hirano, T. Satoh, M. Miura
Org. Lett. 2014, 16, 2892-2895. [Link]
＜Topics＞
2014/12 M2の飯塚君が石油学会関西支部 第23回研究発表会優秀研究賞を受賞しました！
2014/11 M2の小谷さんが第4回CSJ化学フェスタ2014 優秀ポスター発表賞を受賞しました！
2014/10 D1の宇納君が第61回有機金属化学討論会ポスター賞を受賞しました！
2014/7 M2の飯塚君が第26回ICOMC2014 ポスター賞を受賞しました！
2014/7 佐藤准教授、平野助教が第3回大阪大学総長奨励賞を受賞しました！
2014/5 三浦教授、佐藤准教授、平野助教が第13回GSC賞文部科学大臣賞を受賞しました！
2014/4 B4の戒田君が大阪大学未来基金専門教育優秀賞を受賞しました！
2014/4 新しいメンバーが三浦研に加わりました。(B4 5人)
2014/4 三浦教授が大阪大学特別教授の称号を授与されました。
2014/3 B4の高松君、横山君が平成25年度工学賞を受賞しました！
2013/12 M1の鈴木さんが石油学会関西支部 第22回研究発表会優秀ポスター賞を受賞しました！
2013/10 M2の宇納君が第3回CSJ化学フェスタ2013 優秀ポスター発表賞を受賞しました！
2013/9 M2の伊藤君が第9回GSCポスター賞を受賞しました！
2013/8 三浦教授が平成25年度の大阪大学総長顕彰を授与されました。
総長顕彰は、大阪大学に勤務する教員のうち、
教育、研究、社会・国際貢献または管理運営上の業績が
特に顕著であると認められた者に贈られます。
総長顕彰は、大阪大学に勤務する教員のうち、
教育、研究、社会・国際貢献または管理運営上の業績が
特に顕著であると認められた者に贈られます。
2013/2 三浦教授が日本化学会第30回学術賞を受賞しました！(リンク)
2012/2/14 三浦教授・佐藤准教授が『第3回リサーチフロントアワード』を受賞しました！
トムソン・ロイターのプレリリースはこちら
Rhodium(III)-Catalyzed Oxidative Alkenylation of 1,3-Dithiane-Protected Arenecarbaldehydes via Regioselective C-H Bond Cleavage
Y. Unoh, K. Hirano, T. Satoh, M. Miura
Org. Lett. 2015, ASAP. [Link]
Copper-Catalyzed Stereoselective Aminoboration of Bicyclic Alkenes
R. Sakae, K. Hirano, T. Satoh, M. Miura
Angew. Chem. Int. Ed. 2015, 54, 613-617. [Link]
Rhodium-Catalyzed Intramolecular Dehydrogenative Aryl-Aryl Coupling Using Air as Terminal Oxidant
H. Baars, Y. Unoh, T, Okada, K. Hirano, T. Satoh, K, Tanaka, C, Bolm, M. Miura
Chem. Lett. 2014, 43, 1782-1784. [Link]
Iridium-Catalyzed Annulative Coupling of 2-Arylbenzoyl Chlorides with Alkynes: Selective Formation of Phenanthrene Derivatives
T. Nagata, K. Hirano, T. Satoh, M. Miura
J. Org. Chem. 2014, 79, 8960-8967. [Link]
Unexpected Cyclization of Tritylamines Promoted by Copper Salt through C-H and C-N Bond Cleavages to Produce Acridine Derivatives
R. Morioka, K. Hirano, T. Satoh, M. Miura
Chem. Eur. J. 2014, 20, 12720-12724. [Link]
Copper-Mediated C6-Selective Dehydrogenative Heteroarylation of 2-Pyridones with 1,3-Azoles
R. Odani, K. Hirano, T. Satoh, M. Miura
Angew. Chem. Int. Ed. 2014, 53,10784-10788. [Link]
Rhodium(III)-Catalyzed Regioselective C-H Alkenylation of Phenylphosphine Sulfides
Y. Yokoyama, Y, Unoh, K. Hirano, T. Satoh, M. Miura
J. Org. Chem. 2014, 79, 7649-7655. [Link]
2,6-Diphenyl- and -distyryl-capped 3,7-dialkoxybenzo[1,2-b:4,5-b']dithiophenes and their dithieno-annulated higher homologs: structural phase transition with enhanced charge carrier mobility
S. Minami, M. Ide, K. Hirano, T. Satoh, T. Sakurai, K. Kato, M. Tanaka, S. Seki, M. Miura
Phys. Chem. Chem. Phys. 2014, 16, 18805-18812. [Link]
Synthesis of Triarylmethanes by Palladium-Catalyzed C-H/C-O Coupling of Oxazoles and Diarylmethanol Derivatives
S. Tabuchi, K. Hirano, T. Satoh, M. Miura
J. Org. Chem. 2014, 79, 5401-5411. [Link]
Synthesis of [1]benzothieno[3,2-b][1]benzothiophene (BTBT) and its higher homologs through palladium-catalyzed intramolecular decarboxylative arylation
S. Minami, K. Hirano, T. Satoh, M. Miura
Tetrahedron Lett. 2014, 55, 4175-4177. [Link]
Development of Direct Aromatic Coupling Reactions by Transition Metal Catalysis
M. Miura, T. Satoh, K. Hirano
Bull. Chem. Soc. Japan. 2014, 87, 751-764. [Link]
Synthesis of Carbazoles by Copper-Catalyzed Intramolecular C-H/N-H Coupling
K. Takamatsu, K. Hirano, T. Satoh, M. Miura
Org. Lett. 2014, 16, 2892-2895. [Link]
Ruthenium- and Rhodium-Catalyzed Dehydrogenative ortho-Alkenylation of Benzylamines via Free Amino Group Directed C-H Bond Cleavage
C. Suzuki, K. Morimoto, K. Hirano, T. Satoh, M. Miura
Adv. Synth. Catal. 2014, 356, 1521-1526. [Link]
Copper-Catalyzed α-Methylenation of Benzylpyridines Using Dimethylacetamide as One-Carbon Source
M. Itoh, K. Hirano, T. Satoh, M. Miura
Org. Lett. 2014, 16, 2050-2053. [Link]
Copper-Mediated Direct Arylation of Azole Compounds
K. Hirano, M. Miura
Top. Catal. 2014, 57, 878-889. [Link]
Copper-Catalyzed Enantioselective Formal Hydroamination of Oxa- and Azabicyclic Alkenes with Hydrosilanes and Hydroxylamines
Y. Miki, K. Hirano, T. Satoh, M. Miura
Org. Lett. 2014, 16, 1498-1501. [Link]
Highlighted in Synfacts 2014, 10, 0599. [Link]
Rhodium(III)-Catalyzed Ortho-Alkenylation through C-H Bond Cleavage Directed by Sulfoxide Groups
K. Nobushige, K. Hirano, T. Satoh, M. Miura
Org. Lett. 2014, 16, 1188-1191. [Link]
Copper-catalyzed aminoboration and hydroamination of alkenes with electrophilic amination reagents
K. Hirano, M. Miura
Pure Appl. Chem. 2014, 86, 291-297. [Link]
Highly Stereoselective Synthesis of (Borylmethyl)cyclopropylamines by Copper-Catalyzed Aminoboration of Methylenecyclopropanes
R. Sakae, N. Matsuda, K. Hirano, T. Satoh, M. Miura
Org. Lett. 2014, 16, 1228-1231. [Link]
Highlighted in Org. Process Res. Dev. 2014, ASAP. [Link]
Highlighted in Synfacts 2014, 10, 0505. [Link]
Manganese-Mediated C3-Selective Direct Alkylation and Arylation of 2-Pyridones with Diethyl Malonates and Arylboronic Acids
A. Nakatani, K. Hirano, T. Satoh, M. Miura
J. Org. Chem. 2014, 79, 1377-1385. [Link]
Rhodium-Catalyzed Annulative Coupling of 3-Phenylthiophenes with Alkynes Involving Double C-H Bond Cleavages
T. Iitsuka, K. Hirano, T. Satoh, M. Miura
Chem. Eur. J. 2014, 20, 385-389. [Link]
Highlighted in Synfacts 2014, 10, 0265. [Link]
Copper-Mediated Regioselective Homocoupling of Thiophenes and Indoles via Directed C-H Cleavage
R. Odani, M. Nishino, K. Hirano, T. Satoh, M. Miura
Heterocycles 2014, 88, 595-602. [Link]
Palladium-Catalyzed Direct Arylation and Alkenylation of 3-(Indol-3-yl)propionic Acids through C-H Bond Cleavage
D. Takeda, K. Hirano, T. Satoh, M. Miura
Heterocycles 2014, 88, 275-286. [Link]
Rhodium-Catalyzed Decarboxylative and Dehydrogenative Coupling of Maleic Acids with Alkynes and Alkenes
M. Itoh, M. Shimizu, K. Hirano, T. Satoh, M. Miura
J. Org. Chem. 2013, 78, 11427-11432. [Link]
Copper-Mediated Dehydrogenative Biaryl Coupling of Naphthylamines and 1,3-Azoles
R. Odani, K. Hirano, T. Satoh, M. Miura
J. Org. Chem. 2013, 78, 11045-11052. [Link]
An Approach to Benzophosphole Oxides through Silver- or Manganese-Mediated Dehydrogenative Annulation Involving C-C and C-P Bond Formation
Y. Unoh, K. Hirano, T. Satoh, M. Miura
Copper-Catalyzed Intermolecular Regioselective Hydroamination of Styrenes with Polymethylhydrosiloxane and Hydroxylamines
Y. Miki, K. Hirano, T. Satoh, M. Miura
Angew. Chem. Int. Ed. 2013, 52, 10830-10834. [Link]
Highlighted in Synfacts 2013, 9, 1332. [Link]
Highlighted in Angew. Chem. Int. Ed. 2014, 53, 2034-2036. [Link]
Highlighted in Angew. Chem. Int. Ed. 2014, 53, 2034-2036. [Link]
Ruthenium-Catalyzed ortho-Alkenylation of Phenylphosphine Oxides through Regio- and Stereoselective Alkyne Insertion into C-H Bond
M. Itoh, Y. Hashimoto, K. Hirano, T. Satoh, M. Miura
J. Org. Chem. 2013, 78, 8098-8104. [Link]
Ruthenium-Catalyzed Regioselective C-H Alkenylation Directed by a Free Amino Group
C. Suzuki, K. Hirano, T. Satoh, M. Miura
Org. Lett. 2013, 15, 3990-3993. [Link]
Rhodium-Catalyzed C3-Selective Alkenylation of Substituted Thiophene-2-Carboxylic Acids and Related Compounds
T. Iitsuka, P. Schaal, K. Hirano, T. Satoh, C. Bolm, M. Miura
J. Org. Chem. 2013, 78, 7216-7222. [Link]
Highlighted in Synfacts 2013, 9(10), 1064. [Link]
A Formal Anti-Markovnikov Hydroamination of Terminal Aryl Alkynes with Pinacolborane and Hydroxylamines via Zr/Cu Sequential Catalysis
R. Sakae, K. Hirano, T. Satoh, M. Miura
Chem. Lett. 2013, 42, 1128-1130. [Link]
Rhodium(III)-catalyzed Oxidative Coupling through C-H Bond Cleavage Directed by Phosphinoxy Groups
Y. Unoh, Y. Hashimoto, D. Takeda, K. Hirano, T. Satoh, M. Miura
Org. Lett. 2013, 15, 3258-3261. [Link]
C-H Activation of Heteroaromatics
K. Hirano, M. Miura, "Sustainable Catalysis: Challenges and Practices for the Pharmaceutical and Fine Chemical Inductries", Eds. Peter J. Dunn, K. K. (Mimi) Hii, Michael J. Krische, and T. Williams, John Wiley & Sons, Inc., Hoboken, 2013, 233.
Synthesis and properties of a benzo[1,2-b:4,5-b']dithiophene core pi-system that bears alkyl, alkylthio and alkoxy groups at 3,7-positions
S. Ota, S. Minami, K. Hirano, T. Satoh, Y. Ie, S. Seki, Y. Aso, M. Miura
RSC Adv. 2013, 3, 12356-12365. [Link]
Palladium-Catalyzed Decarboxylative Arylation of Benzoylacrylic Acids toward the Synthesis of Chalcones
Y. Unoh, K. Hirano, T. Satoh, M. Miura
J. Org. Chem. 2013, 78, 5096-5102. [Link]
Nickel-Catalyzed Direct Alkylation of Heterocycles with α-Bromo Carbonyl Compounds: C3-Selective Functionalization of 2-Pyridones
A. Nakatani, K. Hirano, T. Satoh, M. Miura
Chem. Eur. J. 2013, 19, 7691-7695. [Link]
Copper-Mediated C-H/C-H Biaryl Coupling of Benzoic Acid Derivatives and 1,3-Azoles
M. Nishino, K. Hirano, T. Satoh, M. Miura
Angew. Chem. Int. Ed. 2013, 52, 4457-4461. [Link]
Highlighted in Synfacts 2013, 9(7), 767. [Link]
Highlighted in Angew. Chem. Int. Ed. 2013, 52, 9896-9898. [Link]
Regioselective and Stereospecific Copper-Catalyzed Aminoboration of Styrenes with Bis(pinacolato)diboron and O-Benzoyl-N,N-dialkylhydroxylamines
N. Matsuda, K. Hirano, T. Satoh, M. Miura
J. Am. Chem. Soc. 2013, 135, 4934-4937. [Link]
Highlighted in Synfacts 2013, 9(7), 757. [Link]
Highlighted in Org. Process Res. Dev. 2013, 17, 952-962. [Link]
Synthesis of N-Vinylcarbazoles via Dehydrogenative Coupling of N-H Carbazoles with Alkenes under Palladium Catalysis
D. Takeda, K. Hirano, T. Satoh, M. Miura
Org. Lett. 2013, 15, 1242-1245. [Link]
Rhodium- and Iridium-Catalyzed Dehydrogenative Cyclization through Double C-H Bond Cleavages To Produce Fluorene Derivatives
M. Itoh, K. Hirano, T. Satoh, Y. Shibata, K. Tanaka, M. Miura
J. Org. Chem. 2013, 78 , 1365-1370. [Link]
,
Synthesis of highly substituted isocoumarins by rhodium-catalyzed annulation of readily available benzoic acids
Y. Unoh, K. Hirano, T. Satoh, M. Miura
Regioselective C-H Bond Cleavage/Alkyne Insertion under Ruthenium Catalysis
Y. Hashimoto, K. Hirano, T. Satoh, F. Kakiuchi, M. Miura
J. Org. Chem. 2013, 78 , 638-646. [Link]
Copper-Catalyzed Electrophilic Amination of Arylsilanes with Hydroxylamines
Y. Miki, K. Hirano, T. Satoh, M. Miura
Org. Lett. 2013, 15, 172-175. [Link]
Highlighted in Synfacts 2013, 9(4), 432. [Link]
Copper-Catalyzed Amination of Ketene Silyl Acetals with Hydroxylamines: Electrophilic Amination Approach to α-Amino Acids
N. Matsuda, K. Hirano, T. Satoh, M. Miura
Angew. Chem. Int. Ed. 2012, 51, 11827-11831. [Link]
Copper-Mediated Oxidative Direct C-C (Hetero)Aromatic Cross-Coupling
K. Hirano, M. Miura
Chem. Commun. 2012, 48, 10704-10714. [Link]
Synthesis of Phenanthridines and Related Compounds by Palladium-Catalyzed Direct Coupling via C-H and N-H Bond Cleavages
Daisuke Takeda, Koji Hirano, Tetsuya Satoh, and Masahiro Miura.
Heterocycles. 2012, 86, 487-496. [Link]
Copper-Mediated and Copper-Catalyzed Cross-Coupling of Indoles and 1,3-Azoles: Double C-H Activation
M. Nishino, K. Hirano, T. Satoh, M. Miura
Angew. Chem. Int. Ed. 2012, 51, 6993-6997. [Link]
Highlighted in Org. Process Res. Dev. 2012, 16, 1574-1581. [Link]
A Concise Access to (Polyfluoroaryl)allenes by Cu-Catalyzed Direct Coupling with Propargyl Phosphates
A. Nakatani, K. Hirano, T. Satoh, M. Miura
Org. Lett. 2012, 14, 2586-2589. [Link]
Synthesis of Fluorene Derivatives through Rhodium-Catalyzed Dehydrogenative Cyclization
K. Morimoto, M. Itoh, K. Hirano, T. Satoh, Y. Shibata, K. Tanaka, M. Miura
Angew. Chem. Int. Ed. 2012, 51, 5359-5362. [Link]
Dehydrogenative Synthesis of C3-Azolylindoles via Copper-Promoted Annulative Direct Coupling of o-Alkynylanilines
Y. Oda, N. Matsuyama, K. Hirano, T. Satoh, M. Miura
Synthesis 2012, 44, 1515-1520. [Link]
Ruthenium(II)-Catalyzed Regio- and Stereoselective Hydroarylation of Alkynes via Directed C-H Functionalization
Y. Hashimoto, K. Hirano, T. Satoh, F. Kakiuchi, M. Miura
Org. Lett. 2012, 14, 2058-2061.[Link]
Copper-Catalyzed Amination of Arylboronates with N,N-Dialkylhydroxylamines
N. Matsuda, K. Hirano, T. Satoh, M. Miura
Angew. Chem. Int. Ed. 2012, 51, 3642-3645. [Link]
Highlighted in Synfacts 2012, 8(7), 772. [Link]
Highlighted in Org. Process Res. Dev. 2012, 16, 1244-1257. [Link]
Copper-Catalyzed Direct Amination of Polyfluoroarenes and Azoles with Hydroxylamines and Its Application to the Synthesis of 3-Aminobenzoheteroles
N. Matsuda, K. Hirano, T. Satoh, M. Miura
Synthesis 2012, 19, 1792-1797. [Link]
Ru/Ag-catalyzed Oxidative Alkenylation of Benzamides and Phenylazoles through Regioselective C-H Bond Cleavage
Y. Hashimoto, T. Ortloff, K. Hirano, T. Satoh, C. Bolm, M. Miura
Chem. Lett. 2012, 41, 151-153. [Link]
Synthesis of N-Azolylindoles by Copper-Catalyzed C-H/N-H Coupling-Annulation Sequence of o-Alkynylanilines
Y. Oda, K. Hirano, T. Satoh, M. Miura
Org. Lett. 2012, 14, 664-667. [Link]
Nickel- and Cobalt-Catalyzed Direct Alkylation of Azoles with N-Tosylhydrazones Bearing Unactivated Alkyl Groups
T. Yao, K. Hirano, T. Satoh, M. Miura
Angew. Chem. Int. Ed. 2012, 51, 775-779. [Link]
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An Annulative Electrophilic Amination Approach to 3-Aminobenzoheteroles
N. Matsuda, K. Hirano, T. Satoh, M. Miura
J. Org. Chem. 2012, 77, 617-625. [Link]
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Synthesis of Isochromene and Related Derivatives by Rhodium-Catalyzed Oxidative Coupling of Benzyl and Allyl Alcohols with Alkynes
K. Morimoto, K. Hirano, T. Satoh, M. Miura
J. Org. Chem. 2011, 76, 9548-9551. [Link]
Ruthenium-catalyzed Oxidative Alkenylation of Arenes via Regioselective C-H Bond Cleavage Directed by a Nitrogen-containing Group
Y. Hashimoto, T. Ueyama, T. Fukutani, K. Hirano, T. Satoh, M. Miura
Chem. Lett. 2011, 40, 1165-1166. [Link]
A remarkable effect of ionic liquids in transition-metal-free aerobic oxidation of benzylic alcohols
Y. Oda, K. Hirano, T. Satoh, S. Kuwabata, M. Miura
Tetrahedron Lett. 2011, 52, 5392-5394. [Link]
Palladium-catalyzed Direct Monoarylation of Thiophene-, Benzothiophene-, and Indoleacetic Acids through Regioselective C-H Bond Cleavage
D. Takeda, M. Yamashita, K. Hirano, T. Satoh, M. Miura
Chem. Lett. 2011, 40, 1015-1017. [Link]
Copper-Catalyzed Oxidative Direct Cyclization of N-Methylanilines with Electron-Deficient Alkenes Using Molecular Oxygen
M. Nishino, K. Hirano, T. Satoh, M. Miura
J. Org. Chem. 2011, 76, 6447-6451. [Link]
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Effect of the Substitution Pattern of Alkyl Side Chain in a Benzodithiophene Core π-System on Intra and Inter-Molecular Charge Carrier Mobility
J. Kumagai, K. Hirano, T. Satoh, S. Seki, M. Miura
J. Phys. Chem. B. 2011, 115, 8446-8452. [Link]
Addition/Correction: J. Phys. Chem. B. 2012, 116, 4115. [Link]
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Copper-Mediated Annulative Direct Coupling of o-Alkynylphenols with Oxadiazoles: A Dehydrogenative Cascade Construction of Biheteroaryls
H. Hachiya, K. Hirano, T. Satoh, M. Miura
Org. Lett. 2011, 13, 3076-3079. [Link]
Rhodium-catalyzed Oxidative Coupling of Benzylamines with Alkynes through Dehydrogenation and Dehydrogenative Cyclization
K. Morimoto, K. Hirano, T. Satoh, M. Miura
Chem. Lett. 2011, 40, 600-602. [Link]
Copper-Catalyzed Direct Amination of Electron-Deficient Arenes with Hydroxylamines
N. Matsuda, K. Hirano, T. Satoh, M. Miura
Org. Lett. 2011, 13, 2860-2863. [Link]
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Rhodium-Catalyzed Regioselective Olefination Directed by a Carboxylic Group
S. Mochida, K. Hirano, T. Satoh, M. Miura
J. Org. Chem. 2011, 76, 3024-3033. [Link]
Copper-Catalyzed Annulative Amination of ortho-Alkynylphenols with Hydroxylamines: Synthesis of 3-Aminobenzofurans by Umpolung Amination Strategy
K. Hirano, T. Satoh, M. Miura
Org. Lett. 2011, 13, 2395-2397. [Link]
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Synthesis of Highly Substituted Acenes through Rhodium-Catalyzed Oxidative Coupling of Arylboron Reagents with Alkynes
T. Fukutani, K. Hirano, T. Satoh, M. Miura
J. Org. Chem. 2011, 76, 2867-2874. [Link]
Synthesis of 1,4-Diarylbuta-1,3-dienes through Palladium- Catalyzed Decarboxylative Coupling of Unsaturated Carboxylic Acids
M. Yamashita, K. Hirano, T. Satoh, M. Miura
Adv. Synth. Catal. 2011, 353, 631-636. [Link]
C─H Functionalization of Heteroarenes Using First─Row Transition Metals: Copper and Nickel Catalyses
K. Hirano, M. Miura
J. Syn. Org. Chem. Jpn. 2011, 69, 252-265. [Link]
Stereospecific Copper-Catalyzed C-H Allylation of Electron-Deficient Arenes with Allyl Phosphates
T. Yao, K. Hirano, T. Satoh, M. Miura
Angew. Chem. Int. Ed. 2011, 50, 2990-2994. [Link]
Direct Carbon-Hydrogen Bond Functionalization of Heterocyclic Compounds
K. Hirano, M. Miura
Synlett. 2011, 3, 294-307. [Link]
Copper-Mediated Intermolecular Direct Biaryl Coupling
M. Kitahara, N. Umeda, K. Hirano, T. Satoh, M. Miura
J. Am. Chem. Soc. 2011, 133, 2160-2162. [Link]
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Ruthenium-Catalyzed Oxidative Vinylation of Heteroarene Carboxylic Acids with Alkenes via Regioselective C-H Bond Cleavage
T. Ueyama, S. Mochida, T. Fukutani, K. Hirano, T. Satoh, M. Miura
Org. Lett. 2011, 13, 706-708. [Link]
Copper-Catalyzed Direct Sulfoximination of Azoles and Polyfluoroarenes under Ambient Conditions
M. Miyasaka, K. Hirano, T. Satoh, R. Kowalczyk, C. Bolm, M. Miura
Org. Lett. 2011, 13, 359-361. [Link]
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Rhodium-Catalyzed Oxidative 1:1, 1:2, and 1:4 Coupling Reactions of Phenylazoles with Internal Alkynes through the Regioselective Cleavages of Multiple C-H Bonds
N. Umeda, K. Hirano, T. Satoh, N. Shibata, H. Sato, M. Miura
J. Org. Chem. 2011, 76, 13-24. [Link]
Synthesis of Stilbene and Distyrylbenzene Derivatives through Rhodium-Catalyzed Ortho-Olefination and Decarboxylation of Benzoic Acids
S. Mochida, K. Hirano, T. Satoh, M. Miura
Org. Lett. 2010, 12, 5776-5779. [Link]
Palladium- and Nickel-Catalyzed Direct Alkylation of Azoles with Unactivated Alkyl Bromides and Chlorides
T. Yao, K. Hirano, T. Satoh, M. Miura
Chem. Eur. J. 2010, 16, 12307-12311. [Link]
Palladium Nanoparticles in Ionic Liquid by Sputter Deposition as Catalysts for Suzuki-Miyaura Coupling in Water
Y. Oda, K. Hirano, K. Yoshii, S. Kuwabata, T. Torimoto, M. Miura
Chem. Lett. 2010, 39, 1069-1071. [Link]
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Oxidative Coupling of Aromatic Substrates with Alkynes and Alkenes under Rhodium Catalysis
T. Satoh, M. Miura
Oxidative Nickel-Air Catalysis in C-H Arylation: Direct Cross-Coupling of Azoles with Arylboronic Acids using Air as Sole Oxidant
H. Hachiya, K. Hirano, T. Satoh, M. Miura
Palladium-Catalyzed Direct Oxidative Alkenylation of Azoles
M. Miyasaka, K. Hirano, T. Satoh, M. Miura
J. Org. Chem. 2010, 75, 5421-5424. [Link]
Transition-Metal-Catalyzed Regioselective Arylation and Vinylation of Carboxylic Acids
T. Satoh, M. Miura
Synthesis. 2010, 20, 3395-3409. [Link]
Rhodium-catalyzed Oxidative Coupling/Cyclization of Benzamides with Alkynes via C-H Bond Cleavage
S. Mochida, N. Umeda, K. Hirano, T. Satoh, M. Miura
Chem. Lett. 2010, 39, 744-746. [Link]
A New Entry of Amination Reagents for Heteroaromatic C-H Bonds: Copper-Catalyzed Direct Amination of Azoles with Chloroamines at Room Temperature
T. Kawano, K. Hirano, T. Satoh, M. Miura
J. Am. Chem. Soc. 2010, 132, 6900-6901. [Link]
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Nickel- and Copper-Catalyzed Direct Alkynylation of Azoles and Polyfluoroarenes with Terminal Alkynes under O2 or Atmospheric Conditions
N. Matsuyama, M. Kitahara, K. Hirano, T. Satoh, M. Miura
Org. Lett. 2010, 12, 2358-2361. [Link]
Rhodium-Catalyzed Oxidative Coupling/Cyclization of 2-Phenylindoles with Alkynes via C-H and N-H Bond Cleavages with Air as the Oxidant
K. Morimoto, K. Hirano, T. Satoh, M. Miura
Org. Lett. 2010, 12, 2068-2071. [Link]
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Nickel-Catalyzed Direct C-H Arylation and Alkenylation of Heteroarenes with Organosilicon Reagents
H. Hachiya, K. Hirano, T. Satoh, M. Miura
Angew. Chem. Int. Ed., 2010, 49, 2202-2205. [Link]
Palladium-Catalyzed Direct Benzylation of Azoles with Benzyl Carbonates
T. Mukai, K. Hirano, T. Satoh, M. Miura
Org. Lett. 2010, 12, 1360-1363. [Link]
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Synthesis of Naphtho[1,8-bc]pyran Derivatives and Related Compounds through Hydroxy Group Directed C-H Bond Cleavage under Rhodium Catalysis
S. Mochida, M. Shimizu, K. Hirano, T. Satoh, M. Miura
Chem. Asian J., 2010, 5, 847-851. [Link]
Room Temperature Direct Alkynylation of 1,3,4-Oxadiazoles with Alkynyl Bromides under Copper Catalysis
T. Kawano, N. Matsuyama, K. Hirano, T. Satoh, M. Miura
J. Org. Chem. 2010, 75, 1764-1766. [Link]
Copper-Mediated Direct Cross-Coupling of 1,3,4-Oxadiazoles and Oxazoles with Terminal Alkynes
M. Kitahara, K. Hirano, H. Tsurugi, T. Satoh, M. Miura
Chem. Eur. J. 2010, 16, 1772-1775. [Link]
Synthesis of α,ω-Diarylbutadienes and -Hexatrienes via Decarboxylative Coupling of Cinnamic Acids with Vinyl Bromides under Palladium Catalysis
M. Yamashita, K. Hirano, T. Satoh, M. Miura
Org. Lett. 2010, 12, 592-595. [Link]
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Synthesis of Substituted Stilbenes via Direct Decarboxylative Coupling of Cinnamic Acids with Arylboronic Acids under Palladium Catalysis
M. Yamashita, K. Hirano, T. Satoh, M. Miura
Chem. Lett. 2010, 39, 68-69. [Link]
Rhodium/Phosphine/Amine-HBr Catalyst System for Highly Selective Cross-Cyclodimerization of Aryl- and Alkylalkynes: Efficient Access to Multisubstituted Naphthalene Derivatives
K. Sakabe, H, Tsurugi, K. Hirano, T. Satoh, M. Miura
Chem. Eur. J. 2010, 16, 445-449. [Link]
Synthesis of 2,3-Diarylbenzo[b]thiophenes via Nickel-Catalyzed Suzuki-Miyaura Cross-Coupling and Palladium-Catalyzed Decarboxylative Arylation
M. Miyasaka, K. Hirano, T. Satoh, M. Miura
Adv. Synth. Catal. 2009, 351, 2683-2688. [Link]
Synthesis of Highly Substituted Naphthalene and Anthracene Derivatives by Rhodium-Catalyzed Oxidative Coupling of Arylboronic Acids with Alkynes
T. Fukutani, K. Hirano, T. Satoh, M. Miura
Fused Ring Construction around Pyrrole, Indole, and Related Compounds via Palladium-Catalyzed Oxidative Coupling with Alkynes
M. Yamashita, H. Horiguchi, K. Hirano, T. Satoh, M. Miura
J. Org. Chem. 2009, 74, 7481-7488. [Link]
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Nickel-Catalyzed Direct Alkynylation of Azoles with Alkynyl Bromides
N. Matsuyama, K. Hirano, T. Satoh, M. Miura
Org. Lett. 2009, 11, 4156-4159. [Link]
Rhodium-Catalyzed Mono- and Divinylation of 1-Phenylpyrazoles and Related Compounds via Regioselective C-H Bond Cleavage
N. Umeda, K. Hirano, T. Satoh, M. Miura
J. Org. Chem. 2009, 74, 7094-7099. [Link]
Rhodium-catalyzed oxidative coupling of aromatic imines with internal alkynes via regioselective C-H bond cleavage
T. Fukutani, N. Umeda, K. Hirano, T. Satoh, M. Miura
Nickel-Catalyzed C-H Alkenylation and Alkylation of 1,3,4-Oxadiazoles with Alkynes and Styrenes
T. Mukai, K. Hirano, T. Satoh, M. Miura
Synthesis of Functionalized α-Pyrone and Butenolide Derivatives by Rhodium-Catalyzed Oxidative Coupling of Substituted Acrylic Acids with Alkynes and Alkenes
S. Mochida, K. Hirano, T. Satoh, M. Miura
J. Org. Chem. 2009, 74, 6295-6298. [Link]
Synthesis of 2,5-diaryloxazoles through van Leusen reaction and copper-mediated direct arylation
T. Yoshizumi, T. Satoh, K. Hirano, D. Matsuo, A. Orita, J. Otera, M. Miura
Tetrahedron Lett., 2009, 50, 3273-3276. [Link]
Copper-Mediated Direct Arylation of 1,3,4-Oxadiazoles and 1,2,4-Triazoles with Aryl Iodides
T. Kawano, T. Yoshizumi, K. Hirano, T. Satoh, M. Miura
Org. Lett. 2009, 11, 3072-3075. [Link]
Synthesis of Condensed Heteroaromatic Compounds by Palladium-Catalyzed Oxidative Coupling of Heteroarene Carboxylic Acids with Alkynes
M. Yamashita, K. Hirano, T. Satoh, M. Miura
Org. Lett. 2009, 11, 2337-2340. [Link]
Palladium-Catalyzed Three-Component 1:2:1 Coupling of Aryl Iodides, Alkynes, and Alkenes to Produce 1,3,5-Hexatriene Derivatives
H, Horiguchi, K. Hirano, T. Satoh, M. Miura
Adv. Synth. Catal. 2009, 351, 1431-1436. [Link]
Nickel- and Rhodium-Catalyzed Addition of Terminal Silylacetylenes to Propargyl Amines Catalyst-Dependent Complementary Regioselectivity
N. Matsuyama, K. Hirano, T. Satoh, M. Miura
J. Org. Chem. 2009, 74, 3576-3578. [Link]
Waste-free Synthesis of Condensed Heterocyclic Compounds by Rhodium-catalyzed Oxidative Coupling of Substituted Arene or Heteroarene Carboxylic Acids with Alkynes
M. Shimizu, K. Hirano, T. Satoh, M. Miura
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Nickel-catalyzed Direct Arylation of Azoles with Aryl Bromides
H. Hachiya, K. Hirano, T. Satoh, M. Miura
Org. Lett. 2009, 11, 1737-1740. [Link]
Fluorescent Diarylindoles by Palladium-Catalyzed Direct and Decarboxylative Arylations of Carboxyindoles
M. Miyasaka, A. Fukushima, T. Satoh, K. Hirano, M. Miura
Chem. Eur. J. 2009, 15, 3674-3677. [Link]
Rhodium-Catalyzed and Coordination-Assisted Regioselective Alkenylation of Aromatic C-H Bonds with Terminal Silylacetylenes
T. Katagiri, T. Mukai, T. Satoh, K. Hirano, M. Miura
Chem. Lett. 2009, 38, 118-119. [Link]
N. Matsuyama, H. Tsurugi, T. Satoh, M. Miura
Adv. Synth. Catal. 2008, 350, 2274-2278. [Link]
Rhodium-catalyzed (E)-selective cross-dimerization of terminal alkynes
T. Katagiri, H. Tsurugi, T. Satoh, M. Miura
Chem. Commun. 2008, 29, 3405-3407. [Link]
Rhodium-Catalyzed Regioselective Arylation of Phenylazoles and Related Compounds with Arylboron Reagents via C-H Bond Cleavage
S. Miyamura, H, Tsurugi, T. Satoh, M. Miura
J. Organomet. Chem. 2008, 693, 2438-2442. [Link]
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