Direct reductive amination using triethylsilane and catalytic bismuth(III) chloride

Takehiko Matsumura, Masahisa Nakada

Research output: Contribution to journalArticle

14 Citations (Scopus)

Abstract

Direct reductive amination (DRA) using triethylsilane (TESH) and catalytic bismuth(III) chloride (BiCl3) is described for the first time. The use of TESH and BiCl3 provides easy handling, low cost, non-toxicity, and a mild Lewis acid activity, thereby meeting the demand for green and sustainable chemistry. The developed DRA is highly chemoselective and applicable to less-basic amines. The experimental results of this study revealed that the developed DRA could be catalyzed by BiCl3, which was gradually reduced to Bi(0) or bismuth with a low valency by TESH, but TESCl, Bi(0), and Bi(0) with TESCl catalyzed the DRA to some extent.

Original languageEnglish
Pages (from-to)1829-1834
Number of pages6
JournalTetrahedron Letters
Volume55
Issue number10
DOIs
Publication statusPublished - 2014 Mar 5

Keywords

  • Bismuth(0)
  • Bismuth(III) chloride
  • Catalysis
  • Direct reductive amination
  • Triethylsilane

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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