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2017 Fiscal Year Annual Research Report

バイオマスの有効利用を指向した光と金属触媒を用いる炭素-炭素結合切断反応の開発

Research Project

Project/Area Number 16F16340
Research InstitutionKyoto University

Principal Investigator

村上 正浩  京都大学, 工学研究科, 教授 (20174279)

Co-Investigator(Kenkyū-buntansha) ZHOU WANG  京都大学, 工学(系)研究科(研究院), 外国人特別研究員
Project Period (FY) 2016-10-07 – 2019-03-31
Keywordsalkene / C-C bond cleavage / photocatalysis / pyridine N-oxide / ortho-alkylation
Outline of Annual Research Achievements

Pyridines are prevalent structural units in drug molecules. Developing methods for the synthesis of alkylated pyridine have attracted an increasing interest since chemical modification of pyridine core, especially at later-stages, will offer a rapid access to the analogues of clinical candidates that is particularly important in the drug discovery process. we have developed a photo-induced alkylation reaction of pyridine N-oxides by using alkenes as alkylating reagents (ACIE, 2018, 57, 5139). This strategy was successfully applied to the reaction of a variety of N-oxides and alkenes, yielding pyridines having benzylic and secondary alkyl groups at the ortho-position.

Current Status of Research Progress
Current Status of Research Progress

2: Research has progressed on the whole more than it was originally planned.

Reason

My research focus now shift to another topic, photo-induced synthesis of alfa-(pyridin-2-yl)styrene from selective coupling between aryl halide and 2-vinylpyridine. Everything is underway as planed.

Strategy for Future Research Activity

For the following fiscal year, we will focus on photo-induced synthesis of alfa-(pyridin-2-yl)styrene from selective coupling between aryl halide and 2-vinylpyridine. The viability of our design will be first tested. If it works, we will turn to the optimal reaction conditions.

  • Research Products

    (3 results)

All 2018 2017

All Journal Article (2 results) (of which Int'l Joint Research: 1 results,  Peer Reviewed: 2 results) Presentation (1 results)

  • [Journal Article] Photo-Catalyzed Ortho-Alkylation of Pyridine N-Oxides through Alkene Cleavage2018

    • Author(s)
      Wang Zhou, Tomoya Miura, Masahiro Murakami
    • Journal Title

      Angewandte Chemie International Edition

      Volume: 印刷中 Pages: 印刷中

    • DOI

      10.1002/anie.201801305

    • Peer Reviewed
  • [Journal Article] Enantioselective Synthesis of anti-1,2-Oxaborinan-3-enes from Aldehydes and 1,1-Di(boryl)alk-3-enes Using Ruthenium and Chiral Phosphoric Acid Catalysts2017

    • Author(s)
      Tomoya Miura, Junki Nakahashi, Wang Zhou, Yota Shiratori, Scott G. Stewart, Masahiro Murakami
    • Journal Title

      Journal of American Chemical Society

      Volume: 139 Pages: 10903-10908

    • DOI

      1021/jacs.7b06408

    • Peer Reviewed / Int'l Joint Research
  • [Presentation] Ortho-Alkylation of Pyridine N-Oxide by Photo-Catalyzed Alkene2018

    • Author(s)
      Wang Zhou
    • Organizer
      日本化学会第98春季年会(2018)

URL: 

Published: 2018-12-17  

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