Cross-Coupling through Selective Cleavage of C-H and C-C Bonds

• Project/Area Number: 20350050
• Research Category: Grant-in-Aid for Scientific Research (B)
• Allocation Type: Single-year Grants
• Section: 一般
• Research Field: Synthetic chemistry
• Research Institution: Osaka University
• Principal Investigator: MIURA Masahiro 大阪大学, 工学研究科, 教授 (20183626)
• Co-Investigator(Renkei-kenkyūsha): SATOH Tetsuya 大阪大学, 工学研究科, 准教授 (40273586) ; HIRANO Koji 大阪大学, 工学研究科, 助教 (70532696)
• Project Period (FY): 2008 – 2010
• Project Status: Completed (Fiscal Year 2010)
• Budget Amount: ¥19,890,000 (Direct Cost: ¥15,300,000、Indirect Cost: ¥4,590,000); Fiscal Year 2010: ¥5,720,000 (Direct Cost: ¥4,400,000、Indirect Cost: ¥1,320,000); Fiscal Year 2009: ¥5,720,000 (Direct Cost: ¥4,400,000、Indirect Cost: ¥1,320,000); Fiscal Year 2008: ¥8,450,000 (Direct Cost: ¥6,500,000、Indirect Cost: ¥1,950,000)
• Keywords: 合成化学 / クロスカップリング / 炭素結合 / 遷移金属触媒 / パイ共役分子

Research Abstract

The coupling reaction of suitably functionalized aromatic and heteroaromatic substrates with aryl halides, alkenes, and alkynes proceeded effectively in the presence of a palladium or rhodium catalyst. Especially, aromatic carboxylic acids was found to undergo multi-coupling via C-H and C-C bond cleavages to afford structurally interesting pi-conjugated compounds. Furthermore, a number of C-H transformation reactions of aromatic compounds by using copper and nickel catalysts have been developed.

Research Products

• [Journal Article] An Annulative Electrophilic Amination Approach to 3-Aminobenzoheteroles (2012)
  • Author(s): Matsuda, Naoki
  • Journal Title: Journal of Organic Chemistry Volume: 77 Pages: 617-625
  • Peer Reviewed
• [Journal Article] Synthesis of Isochromene and Related Derivatives by Rhodium-Catalyzed Oxidative Coupling of Benzyl and Allyl Alcohols with Alkynes (2011)
  • Author(s): Morimoto, K.; Hirano, K.; Satoh, T.; Miura, M.
  • Journal Title: J. Org. Chem Volume: 76 Pages: 9548-9551
• [Journal Article] Ruthenium-catalyzed Oxidative Alkenylation of Arenes via Regioselective C-H Bond Cleavage Directed by a Nitrogen-containing Group (2011)
  • Author(s): Hashimoto, Y.; Ueyama, T.; Fukutani, T.; Hirano, K.; Satoh, T.; Miura, M.
  • Journal Title: Chem. Lett Volume: 40 Pages: 1165-1166
  • NAID: 10029683598
• [Journal Article] Palladium-catalyzed Direct Monoarylation of Thiophene-, Benzothiophene-, and Indoleacetic Acids through Regioselective C-H Bond Cleavage (2011)
  • Author(s): Takeda, D.; Yamashita, M.; Hirano, K.; Satoh, T.; Miura, M.
  • Journal Title: Chem. Lett Volume: 40 Pages: 1015-1017
  • NAID: 10029522707
• [Journal Article] Copper-Catalyzed Oxidative Direct Cyclization of N-Methylanilines with Electron-Deficient Alkenes Using Molecular Oxygen (2011)
  • Author(s): Nishino, M.; Hirano, K.; Satoh, T.; Miura, M.
  • Journal Title: J. Org. Chem Volume: 76 Pages: 6447-6451
• [Journal Article] Copper-Mediated Annulative Direct Coupling of o-Alkynylphenols with Oxadiazoles : A Dehydrogenative Cascade Construction of Biheteroaryls (2011)
  • Author(s): Hachiya, H.; Hirano, K.; Satoh, T.; Miura, M.
  • Journal Title: Org. Lett Volume: 13 Pages: 3076-3079
• [Journal Article] Rhodium-catalyzed Oxidative Coupling of Benzylamines with Alkynes through Dehydrogenation and Dehydrogenative Cyclization (2011)
  • Author(s): Morimoto, K.; Hirano, K.; Satoh, T.; Miura, M.
  • Journal Title: Chem. Lett Volume: 40 Pages: 600-602
  • NAID: 10028243831
• [Journal Article] Copper-Catalyzed Direct Amination of Electron-Deficient Arenes with Hydroxylamines (2011)
  • Author(s): Matsuda, N.; Hirano, K.; Satoh, T.; Miura, M.
  • Journal Title: Org. Lett Volume: 13 Pages: 2860-2863
• [Journal Article] Rhodium-Catalyzed Regioselective Olefination Directed by a Carboxylic Group (2011)
  • Author(s): Mochida, S.; Hirano, K.; Satoh, T.; Miura, M.
  • Journal Title: J. Org. Chem Volume: 76 Pages: 3024-3033
• [Journal Article] Copper-Catalyzed Annulative Amination of ortho-Alkynylphenols with Hydroxylamines : Synthesis of 3-Aminobenzofurans by Umpolung Amination Strategy (2011)
  • Author(s): Hirano, K.; Satoh, T.; Miura, M.
  • Journal Title: Org. Lett Volume: 13 Pages: 2395-2397
• [Journal Article] Synthesis of Highly Substituted Acenes through Rhodium-Catalyzed Oxidative Coupling of Arylboron Reagents with Alkynes (2011)
  • Author(s): Fukutani, T.; Hirano, K.; Satoh, T.; Miura, M.
  • Journal Title: J. Org. Chem Volume: 76 Pages: 2867-2874
• [Journal Article] Synthesis of 1, 4-Diarylbuta-1, 3-dienes through Palladium-Catalyzed Decarboxylative Coupling of Unsaturated Carboxylic Acids (2011)
  • Author(s): Yamashita, M.; Hirano, K.; Satoh, T.; Miura, M.
  • Journal Title: Adv. Synth. Catal Pages: 294-307
• [Journal Article] Direct Carbon-Hydrogen Bond Functionalization of Heterocyclic Compounds (2011)
  • Author(s): Hirano, K.; Miura, M.
  • Journal Title: Synlett Volume: 353 Pages: 631-636
• [Journal Article] Copper-Mediated Intermolecular Direct Biaryl Coupling (2011)
  • Author(s): Kitahara, M.; Umeda, N.; Hirano, K.; Satoh, T.; Miura, M.
  • Journal Title: J. Am. Chem. Soc Volume: 133 Pages: 2160-2162
• [Journal Article] Ruthenium-Catalyzed Oxidative Vinylation of Heteroarene Carboxylic Acids with Alkenes via Regioselective C-H Bond Cleavage (2011)
  • Author(s): Ueyama, T.; Mochida, S.; Fukutani, T.; Hirano, K.; Satoh, T.; Miura, M.
  • Journal Title: Org. Lett Volume: 13 Pages: 706-708
• [Journal Article] Copper-Catalyzed Direct Sulfoximination of Azoles and Polyfluoroarenes under Ambient Conditions (2011)
  • Author(s): Miyasaka, M.; Hirano, K.; Satoh, T.; Kowalczyk, R.; Bolm, C.; Miura, M.
  • Journal Title: Org. Lett Volume: 13 Pages: 359-361
• [Journal Article] 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 (2011)
  • Author(s): Umeda, N.; Hirano, K.; Satoh, T.; Shibata, N.; Sato, H.; Miura, M.
  • Journal Title: J. Org. Chem Volume: 76 Pages: 13-24
• [Journal Article] Synthesis of Isochromene and Related Derivatives by Rhodium-Catalyzed Oxidative Coupling of Benzyl and Allyl Alcohols with Alkynes (2011)
  • Author(s): Morimoto, Keisuke
  • Journal Title: Journal of Organic Chemistry Volume: 76 Pages: 9548-9551
  • Peer Reviewed
• [Journal Article] Ruthenium-catalyzed Oxidative Alkenylation of Arenes via Regioselective C-H Bond Cleavage Directed by a Nitrogen-containing Group (2011)
  • Author(s): Hashimoto, Yuto
  • Journal Title: Chemistry Letters Volume: 40 Pages: 1165-1166
  • Peer Reviewed
• [Journal Article] Palladium-catalyzed Direct Monoarylation of Thiophene-, Benzothiophene-, and Indoleacetic Acids through Regioselective C-H Bond Cleavage (2011)
  • Author(s): Takeda, Daisuke
  • Journal Title: Chemistry Letters Volume: 40 Pages: 1015-1017
  • Peer Reviewed
• [Journal Article] Copper-Catalyzed Oxidative Direct Cyclization of N-Methylanilines with Electron-Deficient Alkenes Using Molecular Oxygen (2011)
  • Author(s): Nishino, Mayuko
  • Journal Title: Journal of Organic Chemistry Volume: 76 Pages: 6447-6451
  • Peer Reviewed
• [Journal Article] Copper-Mediated Annulative Direct Coupling of o-Alkynylphenols with Oxadiazoles : A Dehydrogenative Cascade Construction of Biheteroaryls (2011)
  • Author(s): Hachiya, Hitoshi
  • Journal Title: Organic Letters Volume: 13 Pages: 3076-3079
  • Peer Reviewed
• [Journal Article] Rhodium-catalyzed Oxidative Coupling of Benzylamines with Alkynes through Dehydrogenation and Dehydrogenative Cyclization (2011)
  • Author(s): Morimoto, Keisuke
  • Journal Title: Chemistry Letters Volume: 40 Pages: 600-602
  • Peer Reviewed
• [Journal Article] Copper-Catalyzed Direct Amination of Electron-Deficient Arenes with Hydroxylamines (2011)
  • Author(s): Matsuda, Naoki
  • Journal Title: Organic Letters Volume: 13 Pages: 2860-2863
  • Peer Reviewed
• [Journal Article] Rhodium-Catalyzed Regioselective Olefination Directed by a Carboxylic Group (2011)
  • Author(s): Mochida, Satoshi
  • Journal Title: Journal of Organic Chemistry Volume: 76 Pages: 3024-3033
  • Peer Reviewed
• [Journal Article] Copper-Catalyzed Annulative Amination of ortho-Alkynylphenols with Hydroxylamines : Synthesis of 3-Aminobenzofurans by Umpolung Amination Strategy (2011)
  • Author(s): Hirano, Koji
  • Journal Title: Organic Letters Volume: 13 Pages: 2395-2397
  • Peer Reviewed
• [Journal Article] Synthesis of Highly Substituted Acenes through Rhodium-Catalyzed Oxidative Coupling of Arylboron Reagents with Alkynes (2011)
  • Author(s): Fukutani, Tatsuya
  • Journal Title: Journal of Organic Chemistry Volume: 76 Pages: 2867-2874
  • Peer Reviewed
• [Journal Article] Synthesis of 1,4-Diarylbuta-1,3-dienes through Palladium-Catalyzed Decarboxylative Coupling of Unsaturated Carboxylic Acids (2011)
  • Author(s): Yamashita, Mana
  • Journal Title: Advanced Synthesis & Catalysis Volume: 353 Pages: 631-636
  • Peer Reviewed
• [Journal Article] Direct Carbon-Hydrogen Bond Functionalization of Heterocyclic Compounds (2011)
  • Author(s): Hirano, Koji
  • Journal Title: Synlett Pages: 294-307
  • Peer Reviewed
• [Journal Article] Copper-Mediated Intermolecular Direct Biaryl Coupling (2011)
  • Author(s): Kitahara, Masanori
  • Journal Title: Journal of the American Chemical Society Volume: 133 Pages: 2160-2162
  • Peer Reviewed
• [Journal Article] Ruthenium-Catalyzed Oxidative Vinylation of Heteroarene Carboxylic Acids with Alkenes via Regioselective C-H Bond Cleavage (2011)
  • Author(s): Ueyama, Takumi
  • Journal Title: Organic Letters Volume: 13 Pages: 706-708
  • Peer Reviewed
• [Journal Article] Copper-Catalyzed Direct Sulfoximination of Azoles and Polyfluoroarenes under Ambient Conditions (2011)
  • Author(s): Miyasaka, Mitsuru
  • Journal Title: Organic Letters Volume: 13 Pages: 359-361
  • Peer Reviewed
• [Journal Article] 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 (2011)
  • Author(s): Umeda, Nobuyoshi
  • Journal Title: Journal of Organic Chemistry Volume: 76 Pages: 13-24
  • Peer Reviewed
• [Journal Article] Synthesis of Stilbene and Distyrylbenzene Derivatives through Rhodium-Catalyzed Ortho-Olefination and Decarboxylation of Benzoic Acids (2010)
  • Author(s): Mochida, S.; Hirano, K.; Satoh, T.; Miura, M.
  • Journal Title: Org. Lett Volume: 12 Pages: 5776-5779
• [Journal Article] Palladium-and Nickel-Catalyzed Direct Alkylation of Azoles with Unactivated Alkyl Bromides and Chlorides (2010)
  • Author(s): Yao, T.; Hirano, K.; Satoh, T.; Miura, M.
  • Journal Title: Chem. Eur. J Volume: 16 Pages: 12307-12311
• [Journal Article] Oxidative Coupling of Aromatic Substrates with Alkynes and Alkenes under Rhodium Catalysis (2010)
  • Author(s): Satoh, T.; Miura, M.
  • Journal Title: Chem. Eur. J Volume: 16 Pages: 11212-11222
  • NAID: 120006332334
• [Journal Article] Oxidative Nickel-Air Catalysis in C-H Arylation : Direct Cross-Coupling of Azoles with Arylboronic Acids using Air as Sole Oxidant (2010)
  • Author(s): Hachiya, H.; Hirano, K.; Satoh, T.; Miura, M.
  • Journal Title: ChemCatChem Volume: 2 Pages: 1403-1406
• [Journal Article] Palladium-Catalyzed Direct Oxidative Alkenylation of Azoles (2010)
  • Author(s): Miyasaka, M.; Hirano, K.; Satoh, T.; Miura, M.
  • Journal Title: J. Org. Chem Volume: 75 Pages: 5421-5424
• [Journal Article] Transition-Metal-Catalyzed Regioselective Arylation and Vinylation of Carboxylic Acids (2010)
  • Author(s): Satoh, T.; Miura, M.
  • Journal Title: Synthesis Volume: 20 Pages: 3395-3409
• [Journal Article] Rhodium-catalyzed Oxidative Coupling/ Cyclization of Benzamides with Alkynes via C-H Bond Cleavage (2010)
  • Author(s): Mochida, S.; Umeda, N.; Hirano, K.; Satoh, T.; Miura, M.
  • Journal Title: Chem. Lett Volume: 39 Pages: 744-746
  • NAID: 10027182860
• [Journal Article] Nickel-Catalyzed Direct C-H Arylation and Alkenylation of Heteroarenes with Organosilicon Reagents (2010)
  • Author(s): Hachiya, H.; Hirano, K.; Satoh, T.; Miura, M.
  • Journal Title: Angew. Chem. Int. Ed. Volume: 49 Pages: 2202-2205
• [Journal Article] Copper-Mediated Direct Cross-Coupling of 1, 3, 4-Oxadiazoles and Oxazoles with Terminal Alkynes (2010)
  • Author(s): Kitahara, M.; Hirano, K.; Satoh, T.; Miura, M.
  • Journal Title: Chem. Eur. J Volume: 16 Pages: 1772-1775
• [Journal Article] Synthesis ofα,ω-Diarylbutadienes and-Hexatrienes via Decarboxylative Coupling of Cinnamic Acids with Vinyl Bromides under Palladium Catalysis (2010)
  • Author(s): Yamashita, M.; Hirano, K.; Satoh, T.; Miura, M.
  • Journal Title: Org. Lett Volume: 12 Pages: 592-595
• [Journal Article] Synthesis of Substituted Stilbenes via Direct Decarboxylative Coupling of Cinnamic Acids with Arylboronic Acids under Palladium Catalysis (2010)
  • Author(s): Yamashita, M.; Hirano, K.; Satoh, T.; Miura, M.
  • Journal Title: Chem. Lett Volume: 39 Pages: 68-69
  • NAID: 10027176695
• [Journal Article] Rhodium/ Phosphine/ Amine-HBr Catalyst System for Highly Selective Cross-Cyclodimerization of Aryl-and Alkylalkynes : Efficient Access to Multisubstituted Naphthalene Derivatives (2010)
  • Author(s): Sakabe, K.; Tsurugi, H.; Hirano, K.; Satoh, T.; Miura, M.
  • Journal Title: Chem. Eur. J Volume: 16 Pages: 445-449
• [Journal Article] Synthesis of Stilbene and Distyrylbenzene Derivatives through Rhodium-Catalyzed Ortho-Olefination and Decarboxylation of Benzoic Acids (2010)
  • Author(s): Mochida, Satoshi
  • Journal Title: Organic Letters Volume: 12 Pages: 5776-5779
  • Peer Reviewed
• [Journal Article] Palladium- and Nickel-Catalyzed Direct Alkylation of Azoles with Unactivated Alkyl Bromides and Chlorides (2010)
  • Author(s): Yao, Tomoyuki
  • Journal Title: Chemistry-A European Journal Volume: 16 Pages: 12307-12311
  • Peer Reviewed
• [Journal Article] Palladium Nanoparticles in Ionic Liquid by Sputter Deposition as Catalysts for Suzuki-Miyaura Coupling in Water (2010)
  • Author(s): Oda, Yoshiro
  • Journal Title: Chemistry Letters Volume: 39 Pages: 1069-1071
  • Peer Reviewed
• [Journal Article] Oxidative Coupling of Aromatic Substrates with Alkynes and Alkenes under Rhodium Catalysis (2010)
  • Author(s): Satoh, Tetsuya
  • Journal Title: Chemistry-A European Journal Volume: 16 Pages: 11212-11222
  • Peer Reviewed
• [Journal Article] Palladium-Catalyzed Direct Oxidative Alkenylation of Azoles (2010)
  • Author(s): Miyasaka, Mitsuru
  • Journal Title: Journal of Organic Chemistry Volume: 75 Pages: 5421-5424
  • Peer Reviewed
• [Journal Article] Rhodium-catalyzed Oxidative Coupling/Cyclization of Benzamides with Alkynes via C-H Bond Cleavage (2010)
  • Author(s): Mochida, Satoshi
  • Journal Title: Chemistry Letters Volume: 39 Pages: 744-746
  • Peer Reviewed
• [Journal Article] A New Entry of Amination Reagents for Heteroaromatic C-H Bonds : Copper-Catalyzed Direct Amination of Azoles with Chloroamines at Room Temperature (2010)
  • Author(s): Miura, Masahiro
  • Journal Title: Journal of The American Chemical Society Volume: 132 Pages: 6900-6901
  • Peer Reviewed
• [Journal Article] Nickel- and Copper-Catalyzed Direct Alkynylation of Azoles and Polyfluoroarenes with Terminal Alkynes under O2 or Atmospheric Conditions (2010)
  • Author(s): Miura, Masahiro
  • Journal Title: Organic Letters Volume: 12 Pages: 2358-2361
  • Peer Reviewed
• [Journal Article] Rhodium-Catalyzed Oxidative Coupling/Cyclization of 2-Phenylindoles with Alkynes via C-H and N-H Bond Cleavages with Air as the Oxidant (2010)
  • Author(s): Miura, Masahiro
  • Journal Title: Organic Letters Volume: 12 Pages: 2068-2071
  • Peer Reviewed
• [Journal Article] Nickel-Catalyzed Direct C-H Arylation and Alkenylation of Heteroarenes with Organosilicon Reagents (2010)
  • Author(s): Miura, Masahiro
  • Journal Title: Angewandte Chemie International Edition Volume: 122 Pages: 2248-2251
  • Peer Reviewed
• [Journal Article] Palladium-Catalyzed Direct Benzylation of Azoles with Benzyl Carbonates (2010)
  • Author(s): Miura, Masahiro
  • Journal Title: Organic Letters Volume: 12 Pages: 1360-1363
  • Peer Reviewed
• [Journal Article] Synthesis of Naphtho[1,8-bc]pyran Derivatives and Related Compounds through Hydroxy Group Directed C-H Bond Cleavage under Rhodium Catalysis (2010)
  • Author(s): Miura, Masahiro
  • Journal Title: Chemistry-An Asian Journal Volume: 5 Pages: 847-851
  • Peer Reviewed
• [Journal Article] Room Temperature Direct Alkynylation of 1,3,4-Oxadiazoles with Alkynyl Bromides under Copper Catalysis (2010)
  • Author(s): Miura, Masahiro
  • Journal Title: Journal of Organic Chemistry Volume: 75 Pages: 1764-1766
  • Peer Reviewed
• [Journal Article] Copper-Mediated Direct Cross-Coupling of 1,3,4-Oxadiazoles and Oxazoles with Terminal Alkynes (2010)
  • Author(s): Miura, Masahiro
  • Journal Title: Chemistry-A European Journal Volume: 16 Pages: 1772-1775
  • Peer Reviewed
• [Journal Article] Synthesis of α,ω-Diarylbutadienes and -Hexatrienes via Decarboxylative Coupling of Cinnamic Acids with Vinyl Bromides under Palladium Catalysis (2010)
  • Author(s): Miura, Masahiro
  • Journal Title: Organic Letters Volume: 12 Pages: 592-595
  • Peer Reviewed
• [Journal Article] Synthesis of Substituted Stilbenes via Direct Decarboxylative Coupling of Cinnamic Acids with Arylboronic Acids under Palladium Catalysis (2010)
  • Author(s): Miura, Masahiro
  • Journal Title: Chemistry Letters Volume: 39 Pages: 68-69
  • NAID: 10027176695
  • Peer Reviewed
• [Journal Article] Rhodium/Phosphine/Amine-HBr Catalyst System for Highly Selective Cross-Cyclodimerization of Aryl- and Alkylalkynes : Efficient Access to Multisubstituted Naphthalene Derivatives (2010)
  • Author(s): Miura, Masahiro
  • Journal Title: Chemistry-A European Journal Volume: 16 Pages: 445-449
  • Peer Reviewed
• [Journal Article] Synthesis of 2, 3-Diarylbenzo[ b] thiophenes via Nickel-Catalyzed Suzuki-Miyaura Cross-Coupling and Palladium-Catalyzed Decarboxylative Arylation (2009)
  • Author(s): Miyasaka, M.; Hirano, K.; Satoh, T.; Miura, M.
  • Journal Title: Adv. Synth. Catal Volume: 351 Pages: 2683-2688
• [Journal Article] Synthesis of Highly Substituted Naphthalene and Anthracene Derivatives by Rhodium-Catalyzed Oxidative Coupling of Arylboronic Acids with Alkynes (2009)
  • Author(s): Fukutani, T.; Hirano, K.; Satoh, T.; Miura, M.
  • Journal Title: Org. Lett Volume: 11 Pages: 5198-5201
• [Journal Article] Fused Ring Construction around Pyrrole, Indole, and Related Compounds via Palladium-Catalyzed Oxidative Coupling with Alkynes (2009)
  • Author(s): Yamashita, M.; Horiguchi, H.; Hirano, K.; Satoh, T.; Miura, M.
  • Journal Title: J. Org. Chem Volume: 74 Pages: 7481-7488
• [Journal Article] Nickel-Catalyzed Direct Alkynylation of Azoles with Alkynyl Bromides (2009)
  • Author(s): Matsuyama, M.; Hirano, K.; Satoh, T.; Miura, M.
  • Journal Title: Org. Lett Volume: 11 Pages: 4156-4159
• [Journal Article] Rhodium-Catalyzed Mono-and Divinylation of 1-Phenylpyrazoles and Related Compounds via Regioselective C-H Bond Cleavage (2009)
  • Author(s): Umeda, N.; Hirano, K.; Satoh, T.; Miura, M.
  • Journal Title: J. Org. Chem Volume: 74 Pages: 7094-7099
• [Journal Article] Rhodium-catalyzed oxidative coupling of aromatic imines with internal alkynes via regioselective C-H bond cleavage (2009)
  • Author(s): Fukutani, T.; Umeda, M.; Hirano, K.; Satoh, T.; Miura, M.
  • Journal Title: Chem. Commun Pages: 5141-5143
• [Journal Article] Nickel-Catalyzed C-H Alkenylation and Alkylation of 1, 3, 4-Oxadiazoles with Alkynes and Styrenes (2009)
  • Author(s): Mukai, T.; Hirano, K.; Satoh, T.; Miura, M.
  • Journal Title: J. Org. Chem Volume: 74 Pages: 6410-6413
• [Journal Article] Synthesis of Functionalizedα-Pyrone and Butenolide Derivatives by Rhodium-Catalyzed Oxidative Coupling of Substituted Acrylic Acids with Alkynes and Alkenes (2009)
  • Author(s): Mochida, S.; Hirano, K.; Satoh, T.; Miura, M.
  • Journal Title: J. Org. Chem Volume: 74 Pages: 6295-6298
• [Journal Article] Copper-Mediated Direct Arylation of 1, 3, 4-Oxadiazoles and 1, 2, 4-Triazoles with Aryl Iodides (2009)
  • Author(s): Kawano, T.; Yoshizumi, T.; Hirano, K.; Satoh, T.; Miura, M.
  • Journal Title: Org. Lett Volume: 11 Pages: 3072-3075
• [Journal Article] Synthesis of Condensed Heteroaromatic Compounds by Palladium-Catalyzed Oxidative Coupling o f Heteroarene Carboxylic Acids with Alkynes (2009)
  • Author(s): Yamashita, M.; Hirano, K.; Satoh, T.; Miura, M.
  • Journal Title: Org. Lett Volume: 11 Pages: 2337-2340
• [Journal Article] Palladium-Catalyzed Three-Component 1 : 2 : 1 Coupling of Aryl Iodides, Alkynes, and Alkenes to Produce 1, 3, 5-Hexatriene Derivatives (2009)
  • Author(s): Horiguchi, H.; Hirano, K.; Satoh, T.; Miura, M.
  • Journal Title: Adv. Synth. Catal Volume: 351 Pages: 1431-1436
• [Journal Article] Fluorescent Diarylindoles by Palladium-Catalyzed Direct and Decarboxylative Arylations of Carboxyindoles (2009)
  • Author(s): Miyasaka, M.; Fukushima, A.; Satoh, T.; Hirano, K.; Miura, M.
  • Journal Title: Chem. Eur. J Volume: 15 Pages: 3674-3677
• [Journal Article] Synthesis of 2, 5-Diaryloxazoles through van Leusen Reaction and Copper-Mediated Direct Arylation (2009)
  • Author(s): Yosizumi, T.; Satoh, T.; Hirano, K.; Matsuo, D.; Orita, A.; Otera, J.; Miura, M.
  • Journal Title: Tetrahedron Lett Volume: 50 Pages: 3273-3276
• [Journal Article] Rhodium-Catalyzed and Coordination-Assisted Regioselective Alkenylation of Aromatic C-H Bonds with Terminal Silylacetylenes (2009)
  • Author(s): Katagiri, T.; Mukai, T.; Satoh, T.; Hirano, K.; Miura, M.
  • Journal Title: Chem. Lett Volume: 38 Pages: 118-119
  • NAID: 10025118923
• [Journal Article] Synthesis of 2,3-Diarylbenzo[b]thiophenes via Nickel-Catalyzed Suzuki-Miyaura Cross-Coupling and Palladium-Catalyzed Decarboxylative Arylation (2009)
  • Author(s): Miura, Masahiro
  • Journal Title: Advanced Synthesis & Catalysis Volume: 351 Pages: 2683-2688
  • Peer Reviewed
• [Journal Article] Synthesis of Highly Substituted Naphthalene and Anthracene Derivatives by Rhodium-Catalyzed Oxidative Coupling of Arylboronic Acids with Alkynes (2009)
  • Author(s): Miura, Masahiro
  • Journal Title: Organic Letters Volume: 11 Pages: 5198-5201
  • Peer Reviewed
• [Journal Article] Fused Ring Construction around Pyrrole, Indole, and Related Compounds via Palladium-Catalyzed Oxidative Coupling with Alkynes (2009)
  • Author(s): Miura, Masahiro
  • Journal Title: Journal of Organic Chemistry Volume: 74 Pages: 7481-7488
  • Peer Reviewed
• [Journal Article] Nickel-Catalyzed Direct Alkynylation of Azoles with Alkynyl Bromides (2009)
  • Author(s): Miura, Masahiro
  • Journal Title: Organic Letters Volume: 11 Pages: 4156-4159
  • Peer Reviewed
• [Journal Article] Rhodium-Catalyzed Mono- and Divinylation of 1-Phenylpyrazoles and Related Compounds via Regioselective C-H Bond Cleavage (2009)
  • Author(s): Miura, Masahiro
  • Journal Title: Journal of Organic Chemistry Volume: 74 Pages: 7094-7099
  • Peer Reviewed
• [Journal Article] Rhodium-catalyzed oxidative coupling of aromatic imines with internal alkynes via regioselective C-H bond cleavage (2009)
  • Author(s): Miura, Masahiro
  • Journal Title: Chemical Communications Volume: 34 Pages: 5141-5143
  • Peer Reviewed
• [Journal Article] Nickel-Catalyzed C-H Alkenylation and Alkylation of 1,3,4-Oxadiazoles with Alkynes and Styrenes (2009)
  • Author(s): Miura, Masahiro
  • Journal Title: Journal of Organic Chemistry Volume: 74 Pages: 6410-6413
  • Peer Reviewed
• [Journal Article] Synthesis of Functionalized α-Pyrone and Butenolide Derivatives by Rhodium-Catalyzed Oxidative Coupling of Substituted Acrylic Acids with Alkynes and Alkenes (2009)
  • Author(s): Miura, Masahiro
  • Journal Title: Journal of Organic Chemistry Volume: 74 Pages: 6295-6298
  • Peer Reviewed
• [Journal Article] Copper-Mediated Direct Arylation of 1,3,4-Oxadiazoles and 1,2,4-Triazoles with Aryl Iodides (2009)
  • Author(s): Miura, Masahiro
  • Journal Title: Organic Letters Volume: 11 Pages: 3072-3075
  • Peer Reviewed
• [Journal Article] Synthesis of Condensed Heteroaromatic Compounds by Palladium-Catalyzed Oxidative Coupling of Heteroarene Carboxylic Acids with Alkynes (2009)
  • Author(s): Miura, Masahiro
  • Journal Title: Organic Letters Volume: 11 Pages: 2337-2340
  • Peer Reviewed
• [Journal Article] Nickel-and Rhodium-Catalyzed Addition of Terminal Silylacetylenes to Propareyl Amines Catalyst-Dependent Complementary Regioselectiviy (2009)
  • Author(s): Miura, Masahiro
  • Journal Title: The Journal of Organic Chemistry 74 Pages: 3576-3578
  • Peer Reviewed
• [Journal Article] Waste-free Synthesis of Condensed Heterocyclic Compounds by Rhodium-catalyzed Oxidative Coupling of Substituted Arene or Heteroarene Carboxylic Acids with Alkynes (2009)
  • Author(s): Miura, Masahiro
  • Journal Title: The Journal of Organic Chemistry 74 Pages: 3478-3483
  • Peer Reviewed
• [Journal Article] Nickel-catalyzed Direct Arylation of Azoles with Aryl Bromides (2009)
  • Author(s): Miura, Masahiro
  • Journal Title: Organic Letters 11 Pages: 1737-1740
  • Peer Reviewed
• [Journal Article] Fluorescent Diarylindoles by Palladium-Catalyzed Direct and Decarbonylative Arylations of Carboxyindoles (2009)
  • Author(s): Miura, Masahiro
  • Journal Title: Chemistry-A European Journal 15 Pages: 3674-3677
  • Peer Reviewed
• [Journal Article] Rhodium-Catalyzed and Coordination-Assisted Regioselective Alkenylation of Aromatic C-H Bonds with Terminal Silylacetylenes (2009)
  • Author(s): Miura, Masahiro
  • Journal Title: Chemistry Letters 38 Pages: 118-119
  • NAID: 10025118923
  • Peer Reviewed
• [Journal Article] Rhodium-Catalyzed Regioselective Arylation of Phenylazoles and Related Compounds with Arylboron Reagents via C-H Bond Cleavage (2009)
  • Author(s): Miura, Masahiro
  • Journal Title: Journal of Organometallic Chemistry 693 Pages: 2438-2442
  • Peer Reviewed
• [Journal Article] Rhodium-Catalyzed Regioselective Arylation of Phenyazoles and Related Compounds with Arylboron Reagents via C-H Bond Cleavage (2008)
  • Author(s): Miyamura, S.; Tsurugi, H.; Satoh, T.; Miura, M.
  • Journal Title: J. Organomet. Chem Volume: 693 Pages: 2438-2422
• [Journal Article] Ligand Controlled Cross-Dimerization and-Trimerization of Alkynes under Nickel Cata lysis (2008)
  • Author(s): Matsuyama, N.; Tsutugi, H.; Satoh, T.; Miura, M.
  • Journal Title: Adv. Synth. Catal Volume: 350 Pages: 2274-2278
• [Journal Article] Ligand-Controlled Cross-Dimerization and -Trimerization of Alkynes under Nickel Catalysis (2008)
  • Author(s): Miura, Masahiro
  • Journal Title: Advanced Synthesis, Catalysis 350 Pages: 2274-2278
  • Peer Reviewed
• [Journal Article] (Rhodium-catalyzed (E)-selective cross-dimerization of terminal alkynes (2008)
  • Author(s): Miura, Masahiro
  • Journal Title: Chemical Communications 29 Pages: 3405-3407
  • Peer Reviewed
• [Journal Article] Rhodium-Catalyzed Anti Selective Cross-Addition of Bis(trimethylsilyl)acetylene to Diarylacetylenes via Carbon-Silicon Bond Cleavage (2008)
  • Author(s): Miura, Masahiro
  • Journal Title: Organic Letters 10 Pages: 1751-1754
  • Peer Reviewed
• [Journal Article] Fluorescent Naphthyl- and Anthrylazoles from the Catalytic Coupling of Phenylazoles with Internal Alkynes through the Cleavage of Multiple C-H Bonds (2008)
  • Author(s): Miura, Masahiro
  • Journal Title: Angewandte Chemie International Edition 47 Pages: 4019-4022
  • Peer Reviewed
• [Journal Article] Rhodium-Catalyzed Oxidative Coupling between Salicylaldehydes and Internal Alkynes with C-H Bond Cleavage To Produce 2,3-Disubstituted Chromones (2008)
  • Author(s): Miura, Masahiro
  • Journal Title: Chemistry-An Asian Journal 3 Pages: 881-886
  • Peer Reviewed
• [Journal Article] Palladium-Catalyzed Perarylation of 3-Thiophene- and 3-Furancarboxylic Acids Accompanied by C-H Bond Cleavage and Decarboxylation (2008)
  • Author(s): Miura, Masahiro
  • Journal Title: Organic Letters 10 Pages: 1851-1854
  • Peer Reviewed
• [Presentation] 遷移金属触媒を用いる直接的芳香族カップリング (2011)
  • Author(s): 三浦雅博
  • Organizer: 第72回ファインケミカルズ研究会例会
  • Place of Presentation: 大阪国際交流センター(大阪市)(招待講演)
  • Year and Date: 2011-03-03
• [Presentation] Copper-Mediated Cross-Coupling via C-H Cleavage (2011)
  • Author(s): Miura, M.
  • Organizer: Aachen-Osaka Joint Symposium : Biological and Chemical Approaches to Selective Processes
  • Place of Presentation: RWTH Aachen University, Germany
• [Presentation] Synthesis of fused aromatic- and heteroaromatic compounds via transition-metal-catalyzed oxidative coupling (2011)
  • Author(s): Satoh, Tetsuya
  • Organizer: The 16^<th> IUPAC International Symposium on Organometallic Chemistry Directed Towards Organic Synthesis (OMCOS 16)
  • Place of Presentation: Shanghai, China
• [Presentation] Nickel-catalyzed direct alkynylation of azoles (2011)
  • Author(s): Matsuyama, Naoto
  • Organizer: The 16^<th> IUPAC International Symposium on Organometallic Chemistry Directed Towards Organic Synthesis (OMCOS 16)
  • Place of Presentation: Shanghai, China
• [Presentation] Preparation of palladium nanoparticles in ionic liquids by sputter deposition and its application to Suzuki-Miyaura coupling in water (2011)
  • Author(s): Oda, Yoshiro
  • Organizer: The 16^<th> IUPAC International Symposium on Organometallic Chemistry Directed Towards Organic Synthesis (OMCOS 16)
  • Place of Presentation: Shanghai, China
• [Presentation] Rhodium-catalyzed oxidative coupling of benzylamines with alkynes via dehydrogenative cyclization (2011)
  • Author(s): Morimoto, Keisuke
  • Organizer: The 16^<th> IUPAC International Symposium on Organometallic Chemistry Directed Towards Organic Synthesis (OMCOS 16)
  • Place of Presentation: Shanghai, China
• [Presentation] Transition-metal-catalyzed oxidative coupling of aromatic substrates with unsaturated compounds (2011)
  • Author(s): Satoh, Tetsuya
  • Organizer: International Symposium on Organometallic Chemistry 2011 (ISOMC 2011)
  • Place of Presentation: Osaka, Japan
• [Presentation] 遷移金属触媒を用いる直接的芳香族カップリングの新展開 (2010)
  • Author(s): 三浦雅博
  • Organizer: 第38回オルガノメタリックセミナー(触媒学会)
  • Place of Presentation: 大阪大学
  • Year and Date: 2010-11-22
• [Presentation] 炭素.水素結合切断を経る触媒的芳香族カップリング (2010)
  • Author(s): 三浦雅博
  • Organizer: 平成22年度後期有機合成化学講習会(有機合成化学協会)
  • Place of Presentation: 東京(日本薬学会長井記念館)
  • Year and Date: 2010-11-17
• [Presentation] Transition metal-catalyzed oxidative coupling of aromatic substrates with alkynes and alkenes via C-H and/or C-C bond cleavage (2010)
  • Author(s): Satoh, Tetsuya
  • Organizer: The 2010 International Chemical Congress of Pacific Basin Socienties (Pacifichem 2010)
  • Place of Presentation: Honolulu, Hawaii, USA
• [Presentation] Nickel-catalyzed direct C-H alkynylation of azoles (2010)
  • Author(s): Matsuyama, Naoto
  • Organizer: The 2010 International Chemical Congress of Pacific Basin Socienties (Pacifichem 2010)
  • Place of Presentation: Honolulu, Hawaii, USA
• [Presentation] Palladium-catalyzed decarboxylative coupling of biomass-derived cinnamic acids (2010)
  • Author(s): Satoh, Tetsuya
  • Organizer: The 2010 International Chemical Congress of Pacific Basin Socienties (Pacifichem 2010)
  • Place of Presentation: Honolulu, Hawaii, USA
• [Presentation] Nickel-Catalyzed Direct Alkynylation of Azoles (2010)
  • Author(s): Matsuyama, Naoto
  • Organizer: International Symposium on Environmentally Benign Synthesis
  • Place of Presentation: Osaka University Nakanoshima Center, Osaka, Japan
• [Presentation] Copper- or Nickel-Catalyzed Direct Coupling of Heteroarenes (2010)
  • Author(s): Miura, Masahiro
  • Organizer: 3^<rd> Aachen-Osaka Joint Symposium : Biological and Chemical Approaches to Selective Processes
  • Place of Presentation: RWTH Aachen University, Germany
• [Presentation] Synthesis of Fused Aromatic Compounds via Ttansition-Metal-Catalyzed Oxidative Coupling (2010)
  • Author(s): Satoh, Tetsuya
  • Organizer: 12th Belgian Organic Synthesis Symposium (BOSS XII)
  • Place of Presentation: Namur, Belgium
• [Presentation] パイ共役分子の合成を指向した新規錯体触媒反応の開発 (2009)
  • Author(s): 三浦雅博
  • Organizer: 近畿化学協会ヘテロ原子部会平成21年度第二回懇話会
  • Place of Presentation: 京都市
  • Year and Date: 2009-09-01
• [Presentation] 炭素-水素あるいは炭素-炭素結合の切断を経るクロスカップリング (2009)
  • Author(s): 三浦雅博
  • Organizer: 第14回精密合成化学セミナー
  • Place of Presentation: 北海道大学大学院工学研究科
  • Year and Date: 2009-01-09
• [Presentation] 遷移金属触媒を用いるアレーンおよびアルキンカップリングの新展開 (2009)
  • Author(s): 三浦雅博
  • Organizer: 第42回有機金属若手の会夏の学校(近畿化学協会、有機合成化学協会)
  • Place of Presentation: 岐阜市
• [Presentation] 遷移金属触媒を用いたカップリング反応によるパイ共役分子の合成 (2008)
  • Author(s): 三浦雅博
  • Organizer: 光ナノサイエンス
  • Place of Presentation: 奈良先端科学技術大学院大学
  • Year and Date: 2008-12-17
• [Presentation] Catalytic Coupling Directed by Anionic Oxygen Functions via Cleavage of C-H and C-C Bonds (2008)
  • Author(s): Miura, M.
  • Organizer: 5^<th> Asian-European Symposium on Metal Mediated Efficient Organic Synthesis
  • Place of Presentation: Obernai, France
• [Presentation] Catalytic Coupling Directed by Anionic Oxygen Functions via Cleavage of C-H and C-C Bonds (2008)
  • Author(s): 三浦雅博
  • Organizer: 5th Asian-European Symposium on Metal Mediated Efficient Organic Synthesis
  • Place of Presentation: Obernai, France
• [Book] sp2-炭素-水素結合のアリール化およびアルケニル化,不活性結合・不活性分子の活性化 (2011)
  • Author(s): 佐藤哲也, 三浦雅博
  • Publisher: 化学同人
• [Book] Palladium-Catalyzed Direct Arylation Reactions, in Modern Arylation Methods (2009)
  • Author(s): Miura, M.; Satoh T.
  • Publisher: Wiley-VCH
• [Book] Plladium-Catalyzed Direct Arylation Reactions (2009)
  • Author(s): Miura, Masahiro
  • Total Pages: 27
  • Publisher: Wiley-VCH