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Oxidative amidation from nitroalkane and amine

Research Project

Project/Area Number 16K13942
Research Category

Grant-in-Aid for Challenging Exploratory Research

Allocation TypeMulti-year Fund
Research Field Organic chemistry
Research InstitutionTohoku University

Principal Investigator

Hayashi Yujiro  東北大学, 理学研究科, 教授 (00198863)

Project Period (FY) 2016-04-01 – 2018-03-31
Project Status Completed (Fiscal Year 2017)
Budget Amount *help
¥3,640,000 (Direct Cost: ¥2,800,000、Indirect Cost: ¥840,000)
Fiscal Year 2017: ¥1,820,000 (Direct Cost: ¥1,400,000、Indirect Cost: ¥420,000)
Fiscal Year 2016: ¥1,820,000 (Direct Cost: ¥1,400,000、Indirect Cost: ¥420,000)
Keywordsアミド結合 / 有機化学 / 有機合成 / 酸素
Outline of Final Research Achievements

A mild and convenient oxidative entry into amide formation between readily available nitroalkanes and amines has been developed. This amide coupling procedure can be achieved simply in the presence of iodine, molecular oxygen, and solid potassium carbonate. For peptide synthesis, amidation proceeds with complete stereochemical integrity and high functional group tolerance.
We also developed an efficient amidation method between readily available 1,1-dicyanoalkanes and chiral or non-chiral amines simply with molecular oxygen and a carbonate base. Both oxidative protocols can be applied to sterically and electronically challenging substrates in a highly chemoselective, practical, and rapid manner. Mechanistic investigation reveals that the radical species are involved in both reactions.

Report

(3 results)
  • 2017 Annual Research Report   Final Research Report ( PDF )
  • 2016 Research-status Report
  • Research Products

    (4 results)

All 2016 Other

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

  • [Int'l Joint Research] University of Lincoln(英国)

    • Related Report
      2017 Annual Research Report
  • [Int'l Joint Research] University of Lincoln(英国)

    • Related Report
      2016 Research-status Report
  • [Journal Article] Mechanism of Oxidative Amidation of Nitroalkanes with Oxygen and Amine Nucleophiles by Using Electrophilic Iodine2016

    • Author(s)
      J. Li, M. J. Lear, E. Kwon, Y. Hayashi
    • Journal Title

      Chem. Eur. J.

      Volume: 22 Issue: 16 Pages: 5538-5542

    • DOI

      10.1002/chem.201600540

    • Related Report
      2016 Research-status Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Sterically Demanding Oxidative Amidation of α-Substituted Malononitriles with Amines Using O22016

    • Author(s)
      J. Li, M. J. Lear, Y. Hayashi
    • Journal Title

      Angew. Chem. Int. Ed.

      Volume: 55 Issue: 31 Pages: 9060-9064

    • DOI

      10.1002/anie.201603399

    • Related Report
      2016 Research-status Report
    • Peer Reviewed / Open Access / Int'l Joint Research

URL: 

Published: 2016-04-21   Modified: 2022-06-16  

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