Unsupported Nanoporous Gold-Catalyzed Chemoselective Reduction of Quinolines Using Formic Acid as a Hydrogen Source

Madiha Butt, Yuhui Zhao, Xiujuan Feng, Ye Lu, Tienan Jin, Yoshinori Yamamoto, Ming Bao

Research output: Contribution to journalArticle

Abstract

The unsupported nanoporous gold (AuNPore) is demonstrated to be an active and stable heterogeneous catalyst for chemoselective transfer hydrogenation of quinolines using bio-renewable formic acid (HCO2H) as hydrogen source. The AuNPore-catalyzed transfer hydrogenation of quinolines proceeded smoothly in the presence of low amounts of HCO2H at a relatively low temperature to produce the desired 1,2,3,4-tetrahydroquinolines (py-THQs) in good to excellent yields. Mechanistic studies revealed that the AuNPore-catalyzed transfer hydrogenation of quinolines proceeded through a sequence of 1,4-hydride addition, isomerization, and 1,2-hydride addition. This operationally simple protocol offers a practical alternative to the currently known methods for chemoselective quinoline reduction.

Original languageEnglish
Pages (from-to)6572-6577
Number of pages6
JournalChemistrySelect
Volume4
Issue number21
DOIs
Publication statusPublished - 2019 Jun 7

Keywords

  • 1,2,3,4-tetrahydroquinolines
  • AuNPore
  • HCOH
  • quinoline
  • reduction

ASJC Scopus subject areas

  • Chemistry(all)

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