Palladium-catalyzed picolinamide-directed halogenation of ortho C-H bonds of benzylamine substrates

Chengxi Lu, Shu Yu Zhang, Gang He, William A. Nack, Gong Chen

Research output: Contribution to journalArticle

30 Scopus citations

Abstract

We report a new set of methods for the halogenation of the ortho C-H bonds of N-benzyl picolinamides under palladium-catalyzed conditions. These reactions feature the use of a unique combination of K(Na)XO3 and K 2S2O8 reagents, which enables the installation of iodo, bromo, and chloro groups onto the ortho position of N-benzyl picolinamides in a unified fashion. A variety of benzylamine products bearing complex halogen substitution can be quickly prepared from much simpler precursors in good yield and selectivity.

Original languageEnglish (US)
Pages (from-to)4197-4203
Number of pages7
JournalTetrahedron
Volume70
Issue number27-28
DOIs
StatePublished - Jul 8 2014

    Fingerprint

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this