Exploring the reactivity of halogen-free aminopyridines in one-pot palladium-catalyzed C–N cross-coupling/C–H functionalization

Research output: Contribution to journalArticlepeer-review

1 Citation (Scopus)

Abstract

Aminopyridines are key building blocks for the synthesis of bioactive N-heterocyclic compounds such as azaindoles and imidazopyridines. However, the functionalization of aminopyridines is challenging, due to their electronic properties and coordination with metals. Herein we describe a reactivity study of aminopyridines under palladium-catalyzed reaction conditions. Several aminopyridines underwent a one-pot Pd-catalyzed C–N cross coupling reaction/C–H functionalization sequence affording azaindoles. The role of additives, ligands, and bases was investigated. This work consists of a platform for future studies on aminopyridines involving metal-catalyzed reactions and represents the first report on the direct conversion of non-halogenated aminopyridines into azaindoles via Pd-catalyzed C–H functionalization reactions.

Original languageEnglish
Article number152303
JournalTetrahedron Letters
Volume61
Issue number37
DOIs
Publication statusPublished - 10 Sep 2020

Keywords

  • Aminopyridines
  • Azaindoles
  • Cross-coupling
  • C–H functionalization
  • Pd catalysis

Fingerprint

Dive into the research topics of 'Exploring the reactivity of halogen-free aminopyridines in one-pot palladium-catalyzed C–N cross-coupling/C–H functionalization'. Together they form a unique fingerprint.

Cite this