Tri(1-naphthyl)phosphine as a ligand in palladium-free Sonogashira cross-coupling of arylhalogenides with acetylenes

Anastasiya I. Govdi, Sergey F. Vasilevsky, Svetlana F. Malysheva, Olga N. Kazheva, Oleg A. Dyachenko, Vladimir A. Kuimov

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Abstract

Tri(1-naphthyl)phosphine (Np3P) has been easily prepared in 34% yield from red phosphorus and 1-bromonaphthalene in the superbasic system t-BuONa/DMSO. The expedient procedures for the synthesis of aryl acetylenes by Sonogashira coupling of aryl iodides with terminal alkynes using Np3P as a ligand have been developed. For the first time, it is found that the reaction with compounds containing electron-donating substituents preferably affords buta-1,3-diynes.

Original languageEnglish
Article numbere21443
JournalHeteroatom Chemistry
Volume29
Issue number4
DOIs
Publication statusPublished - 1 Jul 2018
Externally publishedYes

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Keywords

  • 1-bromonaphthalene
  • Sonogashira coupling
  • superbasic system
  • tri(1-naphthyl)phosphine

ASJC Scopus subject areas

  • Chemistry(all)

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