Grant-in-Aid for Scientific Research on Innovative Areas FY2017-2021Hybrid Catalysis

Ryo Shintani » Japanese

Affiliation Graduate School of Engineering Science, Osaka University
Position Professor
Contact Email
HP http://www.chem.es.osaka-u.ac.jp/poc/en/index.html
Speciality Synthetic Organic Chemistry
Keyword Asymmetric Catalysis, Reaction Development
Institute The Chemical Society of Japan; American Chemical Society; The Kinki Chemical Society, Japan; The Society of Synthetic Organic Chemistry, Japan; The Society of Polymer Science, Japan

Abstract

Facile Synthesis of Extended π-Conjugated Molecules under Hybrid Catalysis

Extended π-conjugated organic molecules constitute a class of compounds that can be applied to various useful materials due to their unique electronic and optical properties. In view of available synthetic methods and their efficiency, however, very few practical examples have been developed so far, and accessible molecular structures are still very limited. It is therefore urgently necessary to develop new molecular designs and innovative efficient synthetic methods to realize a breakthrough in this research field.
We recently developed various new synthetic methods under transition-metal catalysis, which allowed for the efficient synthesis of novel extended π-conjugated compounds that are difficult to access with existing methods. But the accessible structures are currently limited with single catalyst systems, and new approaches are required for further progress.
In this context, this research project focuses on the use of hybrid catalyst systems to realize efficient synthesis of functional extended π-conjugated compounds through new types of bond-forming processes that cannot be easily achieved by conventional systems. Specifically, by combining transition-metal catalysis to generate reactive primary products and other catalysis (such as organocatalysis) to convert them to stable final products, we aim to achieve facile construction of one- and two-dimensionally extended π-conjugation systems.

Achievement

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Original papers

  • "Convergent Synthesis of Fluorene Derivatives by Rhodium-Catalyzed Stitching Reaction/Alkene Isomerization Sequence"
    Nishida, M.; *Shintani, R.
    Chem. Eur. J., 4/2019
  • "Synthesis of carbonyl-bridged dibenzofulvalenes and related compounds by rhodium-catalyzed stitching reaction"
    *Shintani, R.; Kishikawa, S.; Nakamura, K.; Tsuda, T.; *Nozaki, K.
    Chem. Commun.,2019, 55(8), 1072-1075
  • "Rhodium-Catalyzed Stitching Polymerization of 1,5-Hexadiynes and Related Oligoalkynes"
    Ikeda, S.; *Shintani, R.
    Angew. Chem., Int. Ed., 3/2019, 58, 5734-5738
  • "Rhodium-Catalyzed Synthesis of Silicon-Bridged 1,2-Dialkenylbenzenes via 1,4-Rhodium Migration"
    Miwa, T.; *Shintani, R.
    Org. Lett., 2/26/2019, 21, 1627–1631

Conference

  • The 1st Sino-Japanese Symposium on Catalysis for Precision Synthesis
    "Synthesis of New π-Conjugated Polymers by Rhodium-Catalyzed Stitching Polymerization of 1,5-Diynes", 口頭発表
    Ikeda, S.; Shintani, R.
    5/28/2019, Shanghai, China
  • 10th Singapore International Chemistry Conference
    "Rhodium-Catalyzed Stitching Reaction for Construction of New Extended π-Conjugation Systems", 招待講演
    Shintani, R.
    12/17/2018, Singapore, Singapore
  • The 18th Tateshina Conference on Organic Chemistry
    "Synthesis of New π-Conjugated Polymers by Rhodium-Catalyzed Stitching Polymerization of 1,5-Diynes", ポスター発表
    Ikeda, S.; Shintani, R.
    11/10/2018, Nagano, Japan
  • The 1st Sino-Japanese Symposium on Catalysis for Precision Synthesis
    "Construction of Extended π-Conjugation Systems by Rhodium-Catalyzed Stitching Reaction", 招待講演
    Shintani, R.
    5/30/2018, Shanghai, China
  • The 1st Sino-Japanese Symposium on Catalysis for Precision Synthesis
    "Synthesis of New π-Conjugated Polymers by Rhodium-Catalyzed Stitching Polymerization of 1,5-Diynes", ポスター発表
    Ikeda, S.; Shintani, R.
    5/29/2018, Shanghai, China

Collaborative Research