Cataltytic CH coupling reactions of heteroaromatic compound and disign of advanced materials with extended ・-conjugation

• Project/Area Number: 22350042
• Research Category: Grant-in-Aid for Scientific Research (B)
• Allocation Type: Single-year Grants
• Section: 一般
• Research Field: Synthetic chemistry
• Research Institution: Kobe University
• Principal Investigator: MORI Atsunori 神戸大学, 大学院・工学研究科, 教授 (90210111)
• Project Period (FY): 2010 – 2012
• Project Status: Completed (Fiscal Year 2012)
• Budget Amount: ¥18,460,000 (Direct Cost: ¥14,200,000、Indirect Cost: ¥4,260,000); Fiscal Year 2012: ¥3,380,000 (Direct Cost: ¥2,600,000、Indirect Cost: ¥780,000); Fiscal Year 2011: ¥3,380,000 (Direct Cost: ¥2,600,000、Indirect Cost: ¥780,000); Fiscal Year 2010: ¥11,700,000 (Direct Cost: ¥9,000,000、Indirect Cost: ¥2,700,000)
• Keywords: 選択的合成 / 反応 / オリゴチオフェン / マグネシウムアミド / ニッケル触媒 / デンドリマー / カップリング反応 / ヘテロ芳香族化合物 / Grignard反応剤 / 多官能性 / チオフェン / チアゾール / ドナー・アクセプター / CHカップリング / 位置選択的 / グラジエント型オリゴチオフェン / リチウムtブトキシド / 塩化アリール / パラジウム触媒

Research Abstract

Catalytic CH coupling reactons forming thiophene-thiophene and thiophene-thiazole bond formation are carried out. Heteroaromatic oligomers of extended pai-conjugation are synthesized with the optimized reaction conditions. Diversity-oriented gradient and donor-acceptor-type oligomeric heteroaromatic compounds are developed directed toward solar cells, semi-conducting organic thin films.

Research Products

• [Journal Article] Concise Synthesis of Well-Defined Linear and Branched Oligothiophenes with Nickel-Catalyzed Regiocontrolled Cross Coupling of 3-Substituted Thiophenes by Catalytically-Generated Magnesium Amide (2013)
  • Author(s): Shota Tanaka, Daiki Tanaka, Go Tatsuta, Kohei Murakami, Shunsuke Tamba, Atsushi Sugie, and Atsunori Mori
  • Journal Title: Chem. Eur. J Volume: 19(5) Issue: 5 Pages: 1658-1665
  • DOI: 10.1002/chem.201203331
  • NAID: 120006220761
  • Peer Reviewed
• [Journal Article] Studies on the preference of multiple coupling in the introduction of thiophene ring into poly-halogenated aromatic compounds with nickel NHC catalyst (2013)
  • Author(s): Shota Tanaka
  • Journal Title: Tetrahedron Letters Volume: 54 Issue: 15 Pages: 1976-1979
  • DOI: 10.1016/j.tetlet.2013.01.127
  • Peer Reviewed
• [Journal Article] Generation of Metalated Thiophenes with Grignard Reagent and Catalytic Secondary Amine for the Cross Coupling Reaction with Aryl Halides (2012)
  • Author(s): Shota Tanaka, Daiki Tanaka, Atsushi Sugie and Atsunori Mori
  • Journal Title: Tetrahedron Lett. Volume: 53 (9) Pages: 1173-1176
  • NAID: 120006220752
  • URL: http://dx.doi.org/10.1016/j.tetlet.2011.12.108.
  • Peer Reviewed
• [Journal Article] C-H Arylation of 3-Substituted Thiophene with Regioselective Deprotonation by TMPMgClLiCl and Transition Metal Catalyzed Cross Coupling (2012)
  • Author(s): Shota Tanaka
  • Journal Title: Heterocycles Volume: 86 Issue: 1 Pages: 255-266
  • DOI: 10.3987/contents-12-86-01
  • Peer Reviewed
• [Journal Article] Shota Tanaka (2012)
  • Author(s): Generation of Metalated Thiophenes with Grignard Reagent and Catalytic Secondary Amine for the Cross Coupling Reaction with Aryl Halides
  • Journal Title: Tetrahedron Letters Volume: 53 Issue: 9 Pages: 1173-1176
  • DOI: 10.1016/j.tetlet.2011.12.108
  • Peer Reviewed
• [Journal Article] Synthesis of Well-defined Head-to-tail-type Oligothiophenes by Regioselective Deprotonation of 3-Substituted Thio-phenes and Nickel-catalyzed Cross Coupling Reaction (2011)
  • Author(s): Shota Tanaka, Shunsuke Tamba, Daiki Tanaka, Atsushi Sugie, Atsunori Mori
  • Journal Title: J. Am. Chem. Soc Volume: 133(42) Issue: 42 Pages: 16734-16737
  • DOI: 10.1021/ja205953g
  • Peer Reviewed
• [Journal Article] C-H Functionalization polycondensation of chlorothiophenes in the presence of nickel catalyst with stoichiometric or catalytically-generated magnesium amide (2011)
  • Author(s): Shunsuke Tamba, Keisuke Shono, Atsushi Sugie, Atsunori Mori
  • Journal Title: J. Am. Chem. Soc Volume: 133(25) Issue: 25 Pages: 9700-9703
  • DOI: 10.1021/ja2033525
  • Peer Reviewed
• [Journal Article] Synthesis and Properties of Seleno-analogue of MK-organic Dye for Photovoltaic Cells Prepared by C-H Functionalization Reactions of Selenophene Derivatives (2011)
  • Author(s): Shunsuke Tamba, Ryosuke Fujii, Atsunori Mori, Kohjiro Hara, and Nagatoshi Koumura
  • Journal Title: Chem. Lett Volume: 40 (9) Pages: 922-924
  • URL: http://dx.doi.org/10.1246/cl.2011.922.
  • Peer Reviewed
• [Journal Article] Cross Coupling on Gold Nanoparticles.Effect of Reinforced Affinity of Organic Group with Bipedal Thiol (2011)
  • Author(s): Atsushi Sugie
  • Journal Title: Chemistry Letters Volume: 40 Issue: 12 Pages: 1450-1452
  • DOI: 10.1246/cl.2011.1450
  • NAID: 10030221816
  • Peer Reviewed
• [Journal Article] Nickel-catalyzed Dehydrobrominative Polycondensation for the Practical Preparation of Regioregular Poly (3-substitutedthiophene)s (2011)
  • Author(s): Shunsuke Tamba
  • Journal Title: Chemistry Letters Volume: 40 Pages: 398-399
  • Peer Reviewed
• [Journal Article] Synthesis and Properties of Seleno-analogue of MK-organic Dye for Photovoltaic Cells Prepared by C-H Functionalization Reactions of Selenophene Derivatives (2011)
  • Author(s): Shunuske Tamba
  • Journal Title: Chemistry Letters Volume: 40 Pages: 922-924
  • Peer Reviewed
• [Journal Article] Palladium-catalyzed C-H Functionalization of Heteroarenes with Aryl Bromides and Chlorides (2010)
  • Author(s): Shunsuke Tamba, Youhei Okubo, Shota Tanaka, Daiki Monguchi, Atsunori Mori
  • Journal Title: J. Org. Chem. Volume: 75 (20) Issue: 20 Pages: 6998-7001
  • DOI: 10.1021/jo101433g
  • Peer Reviewed
• [Journal Article] Iterative Extension of Thiophene Ring Leading to Head-to-tail-type Oligothiophenes via Stepwise CH Arylation and Halogen Exchange Sequence (2010)
  • Author(s): Shunsuke Tanba, Atsushi Sugie, Naoyuki Masuda, Daiki Monguchi, Nagatoshi Koumura, Kohjiro Hara, Atsunori Mori
  • Journal Title: Heterocycles Volume: 82 (1) Issue: 1 Pages: 505-529
  • DOI: 10.3987/com-13-s(s)12
  • NAID: 120006220730
  • Peer Reviewed
• [Presentation] C-H coupling reactions of heteroaromatic compounds by transition-matal catalysis, Atsunori Mori (2013)
  • Author(s): Atsunori Mori
  • Organizer: 4th International conference for Young Chemists 20-13 (4thICYC2013)
  • Place of Presentation: Penang, Malaysia, Keynote Lecture
  • Year and Date: 2013-01-31
• [Presentation] Synthesis of well-defined linear and branched oligothiophenes by regioselective metalation and nickel-catalyzed cross-coupling sequence (2012)
  • Author(s): Atsunori Mori, Shota Tanaka, Daiki Tanaka, Kohei Murakami, Go Tatsuta, Shunsuke Tamba, and Atsushi Sugie
  • Organizer: Cambodian Malaysian Chemical Conference (CMCC) 2012
  • Place of Presentation: Angkor Century Resort & Spa, Siem Reap, Cambodia
• [Presentation] 分岐状オリゴチオフェン合成における多重カップリングの反応性 (2012)
  • Author(s): 立田 豪
  • Organizer: 有機合成化学協会関西支部若手セミナー
  • Place of Presentation: 神戸薬科大学
• [Presentation] Synthesis of well-defined oligothiophene dendrimers by regioselectivedeprotonation and nickel-catalyzed cross coupling (2012)
  • Author(s): Shota Tanaka
  • Organizer: 7th. International Conference on Chemisty of Functional Organic Chemicals
  • Place of Presentation: 東京大学
• [Presentation] オリゴチオフェン，ポリチオフェンの実用的な合成法 (2012)
  • Author(s): 森 敦紀
  • Organizer: 第44回 有機合成セミナー（2012）「新製品創出のための有機合成」
  • Place of Presentation: 大阪市工業研究所
  • Invited
• [Presentation] ニッケル触媒を用いるチオフェンのＣ－Ｈカップリング重合における金属アミドの効果 (2012)
  • Author(s): 丹波俊輔
  • Organizer: 第59回有機金属討論会
  • Place of Presentation: 大阪大学
• [Presentation] 遷移金属触媒を用いた2-ハロ-3-置換チオフェンのC-Hカップリング重合 (2011)
  • Author(s): 丹波俊輔
  • Organizer: 第57回高分子研究発表会(神戸)
  • Place of Presentation: 兵庫県民会館
  • Year and Date: 2011-07-15
• [Presentation] オリゴチオフェン、ポリチオフェンの革新的合成法開発:ヘテロ芳香族 CH 結合でのクロスカップリング反応 (2011)
  • Author(s): 森 敦紀
  • Organizer: 第2回「光・電子材料科学における現状と展望」
  • Place of Presentation: 香川大学工学部
  • Year and Date: 2011-05-27
• [Presentation] オリゴチオフェン、ポリチオフェンの革新的合成法開発:ヘテロ芳香族CH結合でのクロスカップリング反応 (2011)
  • Author(s): 森敦紀
  • Organizer: 第2回「光・電子材料科学における現状と展望」研究会
  • Place of Presentation: 香川大学工学部(香川県)(招待講演)
  • Year and Date: 2011-05-27
• [Book] TCIメール (2012)
  • Author(s): 田中将太
  • Total Pages: 10
  • Publisher: 東京化成工業
• [Book] 有機合成化学協会誌 69 巻,11 号(英文版特集号)1201-1211, Transition metal-catalyzed bond-forming reactions at the C-H bond of heteroaromatic compounds.
  • Author(s): Atsunori Mori
• [Remarks]
  • URL: http://wiki.livedoor.jp/moriorg3/d/Topics?wiki_id=45657
• [Patent(Industrial Property Rights)] ポリチオフェン重合用触媒およびポリ(置換チオフェン)の製造方法 (2010)
  • Inventor(s): 岡本秀二,目黒 晃,森 敦紀
  • Industrial Property Rights Holder: 綜研化学,神戸大学
  • Filing Date: 2010-07-26