• Search Research Projects
  • Search Researchers
  • How to Use
  1. Back to previous page

Development of a nucleophilic deuteration method by using heavy water without any transition metal

Research Project

Project/Area Number 23655030
Research Category

Grant-in-Aid for Challenging Exploratory Research

Allocation TypeMulti-year Fund
Research Field Organic chemistry
Research InstitutionThe University of Tokyo

Principal Investigator

KANO Naokazu  東京大学, 理学(系)研究科(研究院), 准教授 (00302810)

Project Period (FY) 2011 – 2012
Project Status Completed (Fiscal Year 2013)
Budget Amount *help
¥3,640,000 (Direct Cost: ¥2,800,000、Indirect Cost: ¥840,000)
Fiscal Year 2012: ¥1,170,000 (Direct Cost: ¥900,000、Indirect Cost: ¥270,000)
Fiscal Year 2011: ¥2,470,000 (Direct Cost: ¥1,900,000、Indirect Cost: ¥570,000)
Keywordsリン / 同位体標識 / 重水 / 重水素化 / 超原子価 / 極性変換 / 還元 / ヒドリド還元 / 超原子価化合物
Research Abstract

Deuteride reduction reactions of carbonyl compounds were developed by using the umpolung of heavy water under mild conditions without the presence of a transition metal. Ate-type hexacoordinated phosphorus compounds bearing two P-H bonds were synthesized as stable compounds. Two isomers around the phosphorus atom were isolated. Both isomers showed H-D exchange reactivity toward heavy water and hydride reduction reactivity toward carbonyl compounds. The reactivities of one isomer differ from those of the other isomer. Reaction conditions for the one-pot reaction of these two reactions were found, and the carbonyl compounds were formally reduced with heavy water. Therefore, a nucleophilic reductive deuteration method by using heavy water were successfully developed.

Report

(4 results)
  • 2013 Annual Research Report   Final Research Report ( PDF )
  • 2012 Research-status Report
  • 2011 Research-status Report
  • Research Products

    (3 results)

All 2012 2011

All Journal Article (1 results) (of which Peer Reviewed: 1 results) Presentation (2 results)

  • [Journal Article] Isolation of a Metastable Geometrical Isomer of a Hexacoordinated Dihydrophosphate : Elucidation of Its Enhanced Reactivity in Umpolung of a Hydrogen Atom of Wate2011

    • Author(s)
      Hideaki Miyake, Naokazu Kano, Takayuki Kawashima
    • Journal Title

      Inorganic Chemistry

      Volume: 50巻 Issue: 18 Pages: 9083-9089

    • DOI

      10.1021/ic2012765

    • Related Report
      2013 Final Research Report 2011 Research-status Report
    • Peer Reviewed
  • [Presentation] Reductive deuteration of carbonyl compounds with deuterium oxide by using hexacoordinated dihydrophosphates2012

    • Author(s)
      Naokazu Kano, Hideaki Miyake, Takayuki Kawashima
    • Organizer
      The 7th International Conference on Cutting-Edge Organic Chemistry in Asia
    • Place of Presentation
      Nanyang Technological University (Singapore)
    • Related Report
      2013 Final Research Report
  • [Presentation] Reductive Deuteration of Carbonyl Compounds with Deuterium Oxide by Using Hexacoordinated Dihydrophosphates2012

    • Author(s)
      Naokazu Kano, MIyake Hideaki, Takayuki Kawashima
    • Organizer
      The 7th International Conference on Cutting-Edge Organic Chemistry in Asia
    • Place of Presentation
      Singapore
    • Related Report
      2012 Research-status Report

URL: 

Published: 2011-08-05   Modified: 2019-07-29  

Information User Guide FAQ News Terms of Use Attribution of KAKENHI

Powered by NII kakenhi