Nitrile Synthesis by Aerobic Oxidation of Primary Amines and in situ Generated Imines from Aldehydes and Ammonium Salt with Grubbs Catalyst

Tatsuki Utsumi, Kenta Noda, Daichi Kawauchi, Hirofumi Ueda, Hidetoshi Tokuyama

Research output: Contribution to journalArticlepeer-review

4 Citations (Scopus)

Abstract

Herein, a Grubbs-catalyzed route for the synthesis of nitriles via the aerobic oxidation of primary amines is reported. This reaction accommodates a variety of substrates, including simple primary amines, sterically hindered β,β-disubstituted amines, allylamine, benzylamines, and α-amino esters. Reaction compatibility with various functionalities is also noted, particularly with alkenes, alkynes, halogens, esters, silyl ethers, and free hydroxyl groups. The nitriles were also synthesized via the oxidation of imines generated from aldehydes and NH4OAc in situ. (Figure presented.).

Original languageEnglish
Pages (from-to)3583-3588
Number of pages6
JournalAdvanced Synthesis and Catalysis
Volume362
Issue number17
DOIs
Publication statusPublished - 2020 Sep 8

Keywords

  • Grubbs catalyst
  • aerobic oxidation
  • aldehyde
  • amine
  • nitrile

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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