N1-Allylation of Arylhydrazines via a Palladium-Catalyzed Allylic Substitution

Org Lett. 2023 Jul 7;25(26):4880-4885. doi: 10.1021/acs.orglett.3c01684. Epub 2023 Jun 22.

Abstract

A direct and efficient method for constructing N,N-disubstituted hydrazines via a palladium-catalyzed allylic substitution of allyl acetates with arylhydrazines as nucleophiles has been developed. This method is highly selective in terms of both chemo- and regio-selectivity and is carried out under an open-air system with the use of the DPPPy phosphine ligand. Additionally, this reaction is compatible with a wide variety of substrates, including those bearing reactive groups such as Cl, Br, and I, to afford various N1-allylation products in moderate to good yields under simple and mild reaction conditions.

MeSH terms

  • Catalysis
  • Hydrazines*
  • Ligands
  • Molecular Structure
  • Palladium*

Substances

  • Palladium
  • Hydrazines
  • Ligands