Development of Efficient Synthetic Methodologies Based on Direct Functionalization

• Project/Area Number: 21750099
• Research Category: Grant-in-Aid for Young Scientists (B)
• Allocation Type: Single-year Grants
• Research Field: Synthetic chemistry
• Research Institution: The University of Tokyo (2010); Kyoto University (2009)
• Principal Investigator: TAKITA Ryo The University of Tokyo, 大学院・薬学系研究科, 助教 (50452321)
• Project Period (FY): 2009 – 2010
• Project Status: Completed (Fiscal Year 2010)
• Budget Amount: ¥4,420,000 (Direct Cost: ¥3,400,000、Indirect Cost: ¥1,020,000); Fiscal Year 2010: ¥2,340,000 (Direct Cost: ¥1,800,000、Indirect Cost: ¥540,000); Fiscal Year 2009: ¥2,080,000 (Direct Cost: ¥1,600,000、Indirect Cost: ¥480,000)
• Keywords: 触媒反応 / 直接的アリール化反応 / パラジウム / チオフェン / 直接的重合反応 / パラジウム触媒 / ポリチオフェン / ホスフィン配位

Research Abstract

The efficient methodologies based on direct arylation to provide π-conjugate materials has been investigated. A simple catalyst system using Pd(OAc)_2 and 1,10-phenanthroline enables the efficient direct arylation of heteroarenes. Furthermore, the practical dehydrogenative polycondensation of 2-bromothiophenes based on direct arylation method has been developed for the first time to afford polythiophenes with high molecular weight and regioregularity.

Research Products

• [Journal Article] Direct Arylation of Heteroarenes Catalyzed by a Palladium-1,10-Phenanthroline Complex (2011)
  • Author(s): Ryo Takita, Daichi Fujita, Fumiyuki Ozawa
  • Journal Title: Synlett Pages: 959-963
  • Peer Reviewed
• [Journal Article] Direct Arylation of Heteroarenes Catalyzed by a Palladium-1,10-Phenanthroiline Complex (2011)
  • Author(s): Takita, R.; Fujita, D.; Ozawa, F.
  • Journal Title: Synlett Pages: 959-963
  • Peer Reviewed
• [Journal Article] Palladium-Catalyzed Dehydrohalogenative Polycondensation of 2-Bromo-3-hexylthiophene : An Efficient Approach to Head-to-Tail Poly (3-hexylthiophene) (2010)
  • Author(s): Qifeng Wang, Ryo Takita, Yuuta Kikuzaki, Fumiyuki Ozawa
  • Journal Title: J.Am.Chem.Soc. 132 Pages: 11420-11421
  • Peer Reviewed
• [Journal Article] Synthesis and structures of platinum diphenylacetylene and dithiolate complexes bearing diphosphinidenecyclobutene ligands (DPCB-Y) (2010)
  • Author(s): Yumiko Nakajima, Mitsuharu Nakatani, Kyohei Hayashi, Yu Shiraishi, Ryo Takita, Masaaki Okazaki ,Fumiyuki Ozawa
  • Journal Title: New J.Chem. 34 Pages: 1713-1722
  • Peer Reviewed
• [Journal Article] Palladium-Catalyzed Dehydrohalogenative Polycondensation of 2-Bromo-3-hexylthiophene : An Efficient Approach to Head-to-Tail Poly(3-hexylthiophene) (2010)
  • Author(s): Wang, Q.; Takita, R.; Kikuzaki, Y.; Ozawa, F.
  • Journal Title: Journal of the American Chemical Society Volume: 132 Pages: 11420-11421
  • Peer Reviewed
• [Journal Article] Synthesis and structures of platinum diphenylacetylene and dithiolate complexes bearing diphosphinidenecyclobutene ligands (DPCB-Y) (2010)
  • Author(s): Nakajima, Y.; Nakatani, M.; Hayashi, K.; Shiraishi, Y.; Takita, R.; Okazaki, M.; Ozawa, F.
  • Journal Title: New Journal of Chemistry Volume: 34 Pages: 1713-1722
  • Peer Reviewed
• [Journal Article] A Highly Selective Catalytic System for the Cross-Coupling of (E)-Styryl Bromide with Benzeneboronic Acid : Application to the Synthesis of All-trans Poly(arylenevinylene)s (2009)
  • Author(s): Masayuki Wakioka, Yuichiro Mutoh, Ryo Takita, Fumiyuki Ozawa
  • Journal Title: Bulletin of the Chemical Society of Japan 82 Pages: 1292-1298
  • NAID: 10025864802
  • Peer Reviewed
• [Journal Article] The Effects of Primary Structures on Photo-induced Insolubilization of All-cis Poly(p-phenylenevinylene)s in Thin Films (2009)
  • Author(s): Yuichiro Mutoh, Yasutaka Yamamoto, Masayuki Wakioka, Ryo Takita, Jun-ichi Nakamura, Toshiyalida, Fumiyuki Ozawa
  • Journal Title: Bulletin of the Chemical Society of Japan 82 Pages: 1533-1537
  • NAID: 10027170928
  • Peer Reviewed
• [Presentation] アリールパラジウムアセテート錯体によるチオフェン類のC-H結合切断反応 (2011)
  • Author(s): 中村友紀、王奇峰、滝田良、脇岡正幸、小澤文幸
  • Organizer: 日本化学会第91春季年会(発表承認)
  • Place of Presentation: 神奈川(神奈川大学)
  • Year and Date: 2011-03-27
• [Presentation] Direct polymerization of 2-bromothiophenes based on direct arylation reaction (2010)
  • Author(s): Ryo Takita, Qifeng Wang, Yuuta Kikuzaki, Masayuki Wakioka, Fumiyuki Ozawa
  • Organizer: 2010 International Chemical Congress of Pacific Basin Societies (PACIFICHEM 2010)
  • Place of Presentation: アメリカ(ホノルル)
  • Year and Date: 2010-12-17
• [Presentation] Direct polymerization of 2-bromothiophenes based on direct arylation reaction (2010)
  • Author(s): 滝田良、王奇峰、菊崎雄太、中村友紀、脇岡正幸、小澤文幸
  • Organizer: PACIFICHEM 2010
  • Place of Presentation: ホノルル、米国
  • Year and Date: 2010-12-17
• [Presentation] パラジウム触媒による直接的アリール化反応を基軸とする2-ブロモ-3-アルキルチオフェンの重合 (2010)
  • Author(s): 滝田良、王奇峰、菊崎雄太、中村友紀、脇岡正幸、小澤文幸
  • Organizer: 第57回有機金属化学討論会
  • Place of Presentation: 東京(中央大学多摩キャンパス)
  • Year and Date: 2010-09-16
• [Presentation] Palladium-catalyzed Direct Polymerization of 2-Bromothiophenes (2010)
  • Author(s): Ryo Takita, Qifeng Wang, Yuuta Kikuzaki, Yuki Nakamura, Masayuki Wakioka, Fumiyuki Ozawa
  • Organizer: The 24th International Conference on Organometallic Chemistry
  • Place of Presentation: 台湾(台北)
  • Year and Date: 2010-07-22
• [Presentation] 直接的アリール化反応を基軸とするポリチオフェン類の合成 (2010)
  • Author(s): 滝田良、王奇峰、菊崎雄太、中村友紀、小澤文幸
  • Organizer: 日本化学会第90春季年会
  • Place of Presentation: 大阪(近畿大学本部キャンパス)
  • Year and Date: 2010-03-27
• [Presentation] チオフェン類の直接的アリール化反応の開発とその展開 (2009)
  • Author(s): 滝田良、菊崎雄太、王奇峰、藤田大地、小澤文幸
  • Organizer: 第5回物質合成シンポジウム
  • Place of Presentation: 京都(京都大学宇治キャンパス)
  • Year and Date: 2009-11-19
• [Presentation] A New Entry in Palladium-Catalyzed Direct Arylation of Heteroarenes (2009)
  • Author(s): 滝田良, 藤田大地, 小澤文幸
  • Organizer: 15th IUPAC International Symposium on Organometallic Chemistry Directed towards Organic Synthesis (OMCOS 15)
  • Place of Presentation: スコットランド(グラスゴー)
  • Year and Date: 2009-07-27
• [Presentation] A New Entry in Palladium-Catalyzed Direct Arylation of Heteroarenes (2009)
  • Author(s): Ryo Takita, Daichi Fujita, Fumiyuki Ozawa
  • Organizer: 15th IUPAC International Symposium on Organometallic Chemistry Directed towards Organic Synthesis (OMCOS 15)
  • Place of Presentation: 英国、グラスゴー
  • Year and Date: 2009-07-27
• [Remarks] ホームページ等
  • URL: http://www.f.u-tokyo.ac.jp/~kisoyuki/
• [Remarks] 東京大学大学院薬学系研究科・基礎有機化学教室
• [Remarks]
  • URL: http://www.f.u-tokyo.ac.jp/~kisoyuki/
• [Remarks]
  • URL: http://www.kuicr.kyoto-u.ac.jp/icr-bin/KUICR_info.pl?user=takita+ryo