Palladium-Catalyzed sp 3C-H Benzoxylation of Alanine Derivatives Using Aldehydes under Ambient Conditions

Kyalo Stephen Kanyiva*, King Hung Nigel Tang, Jiarui Wang, Takanori Shibata

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

Abstract

The Pd(II)-catalyzed sp 3C-H bond benzoxylation of N -phthaloylalanine derivatives possessing an 8-aminoquinolyl group as a directing group with aldehydes under ambient conditions is reported. When a solution of an alanine derivative and an aldehyde in a toluene/water co-solvent was reacted in the presence of palladium catalyst and tert -butyl hydroperoxide at room temperature, a benzoxylated product was formed in up to 68% yield. The protecting group of the obtained benzoxylated product was smoothly removed to afford a free amide in high yield.

Original languageEnglish
Pages (from-to)3085-3093
Number of pages9
JournalSynthesis (Germany)
Volume53
Issue number17
DOIs
Publication statusPublished - 2021 Sep 1

Keywords

  • C-H bond activation
  • aldehydes
  • benzoxylation
  • palladium
  • α-amino acid derivatives

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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