Catalytic Amination of β-(Hetero)arylethyl Ethers by Phosphazene Base t-Bu-P4

Masanori Shigeno, Ryutaro Nakamura, Kazutoshi Hayashi, Kanako Nozawa-Kumada, Yoshinori Kondo

Research output: Contribution to journalArticlepeer-review

6 Citations (Scopus)

Abstract

We describe the catalytic amination of β-(hetero)arylethyl ethers with amines using the organic superbase t-Bu-P4 to obtain β-(hetero)arylethylamines. The reaction has a broad substrate scope and allows the transformations of electron-deficient and electron-neutral β-(hetero)arylethyl ethers with various amines including pyrrole, N-alkylaniline, diphenylamine, aniline, indole, and indoline derivatives. Mechanistic studies indicate a two-reaction pathway of MeOH elimination from the substrate to form a (hetero)arylalkene followed by the hydroamination of the alkene.

Original languageEnglish
Pages (from-to)6695-6699
Number of pages5
JournalOrganic letters
Volume21
Issue number17
DOIs
Publication statusPublished - 2019 Sep 6

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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