Studies on Cationic Metalloporphyrin Catalyzed Reaction

• Project/Area Number: 23655035
• Research Category: Grant-in-Aid for Challenging Exploratory Research
• Allocation Type: Multi-year Fund
• Research Field: Organic chemistry
• Research Institution: Kyoto University
• Principal Investigator: KURAHASHI Takuya 京都大学, 大学院・工学研究科, 准教授 (50432365)
• Project Period (FY): 2011 – 2012
• Project Status: Completed (Fiscal Year 2012)
• Budget Amount: ¥3,900,000 (Direct Cost: ¥3,000,000、Indirect Cost: ¥900,000); Fiscal Year 2012: ¥1,820,000 (Direct Cost: ¥1,400,000、Indirect Cost: ¥420,000); Fiscal Year 2011: ¥2,080,000 (Direct Cost: ¥1,600,000、Indirect Cost: ¥480,000)
• Keywords: ポルフィリン / 遷移金属 / 触媒反応 / 鉄 / 複素環 / 環化付加反応 / カチオン / ピラン環 / ルイス酸 / 触媒

Research Abstract

The transition metal catalyzed reaction is a useful transformation to prepare complicated compounds in a single step. Ｗe developed unprecedented type of transition metal catalyzed reaction by means of cationic metalloporpyrin complexes.

Research Products

• [Journal Article] Catalytic Asymmetric Aldol-Type Reaction of Zinc Enolate Equivalent of Amides (2013)
  • Author(s): Haraguchi, R.; Matsubara, S.
  • Journal Title: Org. Lett. Volume: 15 Issue: 8 Pages: 3378-3380
  • DOI: 10.1021/ol4005068
  • Peer Reviewed
• [Journal Article] Synthesis of Quinolones by Nickel-Catalyzed Cycloaddition via Elimination of Nitrile (2013)
  • Author(s): Nakai, K.; Kurahashi, T.; Matsubara, S.
  • Journal Title: Org. Lett. Volume: 15 Issue: 4 Pages: 856-859
  • DOI: 10.1021/ol303546p
  • Peer Reviewed
• [Journal Article] Cationic Iron(III) Porphyrin-Catalyzed [4+2] Cycloaddition of Unactivated Aldehydes with Simple Dienes (2012)
  • Author(s): Fujiwara, K.; Kurahashi, T.;Matsubara, S
  • Journal Title: J. Am. Chem. Soc Volume: 134 Issue: 12 Pages: 5512-5515
  • DOI: 10.1021/ja300790x
  • Peer Reviewed
• [Journal Article] Cobalt(III) Porphyrin Catalyzed Aza-Diels-Alder Reaction (2012)
  • Author(s): Wakabayashi, R.; Kurahashi, T.; Matsubara, S
  • Journal Title: Org. Lett Volume: 14(18) Issue: 18 Pages: 4794-4797
  • DOI: 10.1021/ol3020946
  • Peer Reviewed
• [Journal Article] Manganese Porphyrin Catalyzed Cycloisomerization of Enynes (2012)
  • Author(s): 小澤卓也、倉橋拓也、松原誠二郎
  • Journal Title: Org. Lett. Volume: 14 Issue: 12 Pages: 3008-3011
  • DOI: 10.1021/ol301416f
• [Journal Article] Ruthenium Porphyrin Catalyzed Friedel-Crafts Type Reaction Of Arenes With Imines, Terada (2012)
  • Author(s): T.; Kurahashi, T.; Matsubara, S
  • Journal Title: Heterocycles Volume: 85 (10) Issue: 10 Pages: 2415-2415
  • DOI: 10.3987/com-12-12556
  • Peer Reviewed
• [Journal Article] Nickel-Catalyzed [4+2] Cycloaddition (2012)
  • Author(s): Horie, H.; Kurahashi, T.; Matsubara, S.
  • Journal Title: Chem. Commun. Volume: 48 Pages: 3866-3868
  • Peer Reviewed
• [Journal Article] Dehydrogenative Diels-Alder Reaction (2011)
  • Author(s): Ozawa, T.; Kurahashi, T.; Matsubara, S.
  • Journal Title: Org. Lett. Volume: 13 (19) Issue: 19 Pages: 5390-5393
  • DOI: 10.1021/ol202283d
  • Peer Reviewed
• [Journal Article] Nickel-Catalyzed Cycloaddition of o-Arylcarboxybenzonitriles and Alkynes via Cleavage of Two Carbon-Carbon σ Bonds (2011)
  • Author(s): Nakai, K.; Kurahashi, T.; Matsubara, S.
  • Journal Title: J. Am. Chem. Soc. Volume: 133(29) Issue: 29 Pages: 11066-11067
  • DOI: 10.1021/ja203829j
  • Peer Reviewed
• [Journal Article] Nickel-Catalyzed Cycloaddition (2011)
  • Author(s): Horie, H.; Kurahashi, T.; Matsubara, S.
  • Journal Title: Angew. Chem. Int. Ed. Volume: 50 Pages: 8956-8958
  • Peer Reviewed
• [Journal Article] Methylenecyclopropane as C1 Synthetic Units (2011)
  • Author(s): Inami, T.; Kurahashi, T.; Matsubara, S.
  • Journal Title: Chem. Commun. Volume: 47 Pages: 9711-9713
  • Peer Reviewed
• [Journal Article] Nickel-Catalyzed Decarboxylative Polymerization (2011)
  • Author(s): Yoshino, Y.; Kurahashi, T.; Matsubara, S.
  • Journal Title: Chem. Lett. Volume: 40 Pages: 1240-1241
  • Peer Reviewed
• [Journal Article] Nickel-Catalyzed Heteroannulation (2011)
  • Author(s): Yoshida, Y.; Kurahashi, T.; Matsubara, S.
  • Journal Title: Chem. Lett. Volume: 40 Pages: 1067-1068
  • Peer Reviewed
• [Journal Article] Dehydrogenative Diels-Alder Reaction (2011)
  • Author(s): Ozawa, T.; Kurahashi, T.; Matsubara, S.
  • Journal Title: Org. Lett. Volume: 13 Pages: 5390-5394
  • Peer Reviewed
• [Journal Article] Methylenecyclopropanes in [4 + 1] Cycloaddition (2011)
  • Author(s): Inami, T.; Sako, S.; Kurahashi, T.; Matsubara, S.
  • Journal Title: Org. Lett. Volume: 13 Pages: 3837-3840
  • Peer Reviewed
• [Journal Article] Nickel-Catalyzed Cycloaddition (2011)
  • Author(s): Yoshida, Y.; Kurahashi, T.; Matsubara, S.
  • Journal Title: Chem. Lett. Volume: 40 Pages: 1140-1142
  • Peer Reviewed
• [Journal Article] Nickel-Catalyzed [3 + 2] Cycloaddition (2011)
  • Author(s): Sako, S.; Kurahashi, T.; Matsubara, S.
  • Journal Title: Chem. Lett. Volume: 40 Pages: 808-809
  • Peer Reviewed
• [Journal Article] Nickel-Catalyzed [4+2] Cycloaddition (2011)
  • Author(s): Sako, S.; Kurahashi, T.; Matsubara, S.
  • Journal Title: Chem. Commun. Volume: 47 Pages: 6150-6152
  • Peer Reviewed
• [Journal Article] Nickel-Catalyzed Intermolecular Codimerization (2011)
  • Author(s): Horie, H.; Kurahashi, T.; Matsubara, S.
  • Journal Title: Chem. Commun. Volume: 47 Pages: 2658-2660
  • Peer Reviewed
• [Journal Article] Nickel-Catalyzed Cycloadditions (2011)
  • Author(s): Inami, T.; Kurahashi, T.; Matsubara, S.
  • Journal Title: Org. Lett. Volume: 13 Pages: 1912-1915
  • Peer Reviewed
• [Journal Article] Decarbonylative Cycloaddition (2011)
  • Author(s): Ochi, Y.; Kurahashi, T.; Matsubara, S.
  • Journal Title: Org. Lett. Volume: 13 Pages: 1374-1376
  • Peer Reviewed
• [Journal Article] Nickel-Catalyzed Cycloadditions (2011)
  • Author(s): Maizuru,N.; Inami,T.; Kurahashi,T.; Matsubara,S.
  • Journal Title: Org. Lett. Volume: 13 Pages: 1206-1208
  • Peer Reviewed
• [Journal Article] Nickel-Catalyzed Cycloadditions (2011)
  • Author(s): Maizuru,N.; Inami,T.; Kurahashi,T.; Matsubara,S.
  • Journal Title: Chem. Lett. Volume: 40 Pages: 375-376
  • Peer Reviewed
• [Journal Article] Nickel-Catalyzed Decarbonylative Cycloaddition (2011)
  • Author(s): Fujiwara, K.; Kurahashi, T.; Matsubara, S.
  • Journal Title: Chem. Lett. Volume: 40 Pages: 322-323
  • Peer Reviewed
• [Presentation] Phosphine-Mediated Cycloaddition of Thiophtalic Anhydrides with Polyynes (2013)
  • Author(s): 井波輔、倉橋拓也、松原誠二郎
  • Organizer: 日本化学会第93春季年会
  • Place of Presentation: 立命館大学びわこ・くさつキャンパス
  • Year and Date: 2013-03-22
• [Presentation] Iron-Porphinoid-Catalyzed Hetero Diels-Alder Reaction by Dienes and Aldehydes (2013)
  • Author(s): 桑野徹、倉橋拓也、松原誠二郎
  • Organizer: 日本化学会第93春季年会
  • Place of Presentation: 立命館大学びわこ・くさつキャンパス
  • Year and Date: 2013-03-22
• [Presentation] Iron-Porphyrin-Catalyzed [3+2] Cycloaddition Reaction by Aziridines and Carbonyl Compounds (2013)
  • Author(s): 寺西覚、倉橋拓也、松原誠二郎
  • Organizer: 日本化学会第93春季年会
  • Place of Presentation: 立命館大学びわこ・くさつキャンパス
  • Year and Date: 2013-03-22
• [Presentation] Diels-Alder Reaction Catalyzed byCationic Ruthenium Porphyrin Complex (2013)
  • Author(s): 寺田拓真、倉橋拓也、松原誠二郎
  • Organizer: 日本化学会第93春季年会
  • Place of Presentation: 立命館大学びわこ・くさつキャンパス
  • Year and Date: 2013-03-22
• [Presentation] Palladium Porphyrin Catalyzed Hydrogenation (2013)
  • Author(s): 西林亮、倉橋拓也、松原誠二郎
  • Organizer: 日本化学会第93春季年会
  • Place of Presentation: 立命館大学びわこ・くさつキャンパス
  • Year and Date: 2013-03-22
• [Presentation] Nickel-Catalyzed Cycloaddition via Elimination of Carbon Monoxide and Carbon Dioxide (2013)
  • Author(s): 中井健一朗、倉橋拓也、松原誠二郎
  • Organizer: 日本化学会第93春季年会
  • Place of Presentation: 立命館大学びわこ・くさつキャンパス
  • Year and Date: 2013-03-22
• [Presentation] Platinum Porphyrin Catalyzed Cycloisomerization of Enynes (2013)
  • Author(s): 長谷川誠、倉橋拓也、松原誠二郎
  • Organizer: 日本化学会第93春季年会
  • Place of Presentation: 立命館大学びわこ・くさつキャンパス
  • Year and Date: 2013-03-22
• [Presentation] Nickel-Catalyzed Cycloaddition via Elimination of Small Molecule (2012)
  • Author(s): 倉橋拓也、松原誠二郎
  • Organizer: ICCCS-3
  • Place of Presentation: 中華人民共和国杭州大学
  • Year and Date: 2012-11-01
• [Presentation] Synthesis of Ruthenium Porphyrin Complexes and their Application in Organic Synthesis (2012)
  • Author(s): 寺田拓真、倉橋拓也、松原誠二郎
  • Organizer: 第23回基礎有機化学討論会
  • Place of Presentation: 京都テルサ
  • Year and Date: 2012-09-19
• [Presentation] Synthesis of Iron Porphyrin Complexes and their Application in Organic Synthesis (2012)
  • Author(s): 寺西覚、倉橋拓也、松原誠二郎
  • Organizer: 第23回基礎有機化学討論会
  • Place of Presentation: 京都テルサ
  • Year and Date: 2012-09-19
• [Presentation] Cationic Metalloporphyrin-Catalyzed [4+2] Cycloaddition (2012)
  • Author(s): 倉橋拓也、藤原恭平、松原誠二郎
  • Organizer: 第59回有機金属化学討論会
  • Place of Presentation: 大阪大学吹田キャンパス
  • Year and Date: 2012-09-14
• [Presentation] Nickel-catalyzed Cycloaddition via Elimination of Nitrile (2012)
  • Author(s): 中井健一朗、倉橋拓也、松原誠二郎
  • Organizer: 第59回有機金属化学討論会
  • Place of Presentation: 大阪大学吹田キャンパス
  • Year and Date: 2012-09-14
• [Presentation] Nickel-catalyzed Decarbonylative Cycloaddition with Thioisatins: Acceleration of Decarbonylation by Sulfur Coordination (2012)
  • Author(s): 井波輔、倉橋拓也、松原誠二郎
  • Organizer: 第59回有機金属化学討論会
  • Place of Presentation: 大阪大学吹田キャンパス
  • Year and Date: 2012-09-14
• [Presentation] Nickel-Catalyzed Decarbonylative Cycloaddition of Thioisatins to Alkynes (2012)
  • Author(s): 井波輔、倉橋拓也、松原誠二郎
  • Organizer: 日本化学会第92春季年会
  • Place of Presentation: 慶應義塾大学日吉キャンパス
  • Year and Date: 2012-03-25
• [Presentation] Nickel-Catalyzed Coupling Reaction of Aldehydes and Alkynes (2012)
  • Author(s): 吉田有次、倉橋拓也、松原誠二郎
  • Organizer: 日本化学会第92春季年会
  • Place of Presentation: 慶應義塾大学日吉キャンパス
  • Year and Date: 2012-03-25
• [Presentation] Iron-Porphyrin-Catalyzed Friedel-Crafts Reaction with Dehydration by Alcohols and Arenes (2012)
  • Author(s): 寺西覚、倉橋拓也、松原誠二郎
  • Organizer: 日本化学会第92春季年会
  • Place of Presentation: 慶應義塾大学日吉キャンパス
  • Year and Date: 2012-03-25
• [Presentation] Synthesis of Ruthenium Porphyrin Complexes and their Application (2012)
  • Author(s): 寺田拓真、倉橋拓也、松原誠二郎
  • Organizer: 日本化学会第92春季年会
  • Place of Presentation: 慶應義塾大学日吉キャンパス
  • Year and Date: 2012-03-25
• [Presentation] Nickel-catalyzed Decarbonylative Cycloaddition of Phthalimides with Alkynes via gem- Carboamination (2012)
  • Author(s): 芝隆宏、倉橋拓也、松原誠二郎
  • Organizer: 日本化学会第92春季年会
  • Place of Presentation: 慶應義塾大学日吉キャンパス
  • Year and Date: 2012-03-25
• [Presentation] Nickel-catalyzed Decarbonylative Polymerizations of Alkynyl Phthalimide and Phthalic Anhydride (2012)
  • Author(s): 竹内真、倉橋拓也、松原誠二郎
  • Organizer: 日本化学会第92春季年会
  • Place of Presentation: 慶應義塾大学日吉キャンパス
  • Year and Date: 2012-03-25
• [Presentation] Nickel-Catalyzed Cycloaddition via Elimination of Nitrile (2012)
  • Author(s): 中井健一朗、倉橋拓也、松原誠二郎
  • Organizer: 日本化学会第92春季年会
  • Place of Presentation: 慶應義塾大学日吉キャンパス
  • Year and Date: 2012-03-25
• [Presentation] Nickel-Catalyzed [3+2] Cycloaddition of Vinylcyclopropanes and Allenes (2012)
  • Author(s): 頓部李歩子、倉橋拓也、松原誠二郎
  • Organizer: 日本化学会第92春季年会
  • Place of Presentation: 慶應義塾大学日吉キャンパス
  • Year and Date: 2012-03-25
• [Presentation] Creation of Reactive Intermediates from Low-valent Nickel Complexes and Carbonyl Compounds: Their Application for Catalytic Organic Synthesis (2012)
  • Author(s): 倉橋拓也
  • Organizer: 日本化学会第92春季年会
  • Place of Presentation: 慶應義塾大学日吉キャンパス
  • Year and Date: 2012-03-25
• [Presentation] 進歩賞受賞講演 (2012)
  • Author(s): 倉橋拓也
  • Organizer: 日本化学会(招待講演)
  • Place of Presentation: 慶応大学
• [Presentation] Nickel-Catalyzed Cycloaddition of α,β,γ,δ-Unsaturated Ketones with Alkynes (2011)
  • Author(s): 堀江宏彰、倉橋拓也、松原誠二郎
  • Organizer: 第58回有機金属化学討論会
  • Place of Presentation: 名古屋大学東山キャンパス
  • Year and Date: 2011-09-07
• [Presentation] Nickel-Catalyzed Cycloaddition of Thiophthalic Anhydrides with Methylenecyclopropanes to Form Thiophthalides; New Use for Methylenecyclopropane as C1 Synthetic Units (2011)
  • Author(s): 井波輔、倉橋拓也、松原誠二郎
  • Organizer: 第58回有機金属化学討論会
  • Place of Presentation: 名古屋大学東山キャンパス
  • Year and Date: 2011-09-07
• [Presentation] Nicke-Catalyzed Cycloaddition via Cleavage of Two Carbon-Carbon s Bonds (2011)
  • Author(s): 中井健一朗、倉橋拓也、松原誠二郎
  • Organizer: 第58回有機金属化学討論会
  • Place of Presentation: 名古屋大学東山キャンパス
  • Year and Date: 2011-09-07
• [Book] [4+2] Cycloaddition via Metallacycles (2012)
  • Author(s): 倉橋拓也、松原誠二郎
  • Publisher: Transition-Metal-Mediated Aromatic Ring Construction, Wiley(in press)