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

Research output: Contribution to journalArticle

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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phosphine
Alkynes
Palladium
Diynes
Ligands
Iodides
Dimethyl Sulfoxide
Phosphorus
Electrons

Keywords

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

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Tri(1-naphthyl)phosphine as a ligand in palladium-free Sonogashira cross-coupling of arylhalogenides with acetylenes. / Govdi, Anastasiya I.; Vasilevsky, Sergey F.; Malysheva, Svetlana F.; Kazheva, Olga N.; Dyachenko, Oleg A.; Kuimov, Vladimir A.

In: Heteroatom Chemistry, Vol. 29, No. 4, e21443, 01.07.2018.

Research output: Contribution to journalArticle

Govdi, Anastasiya I. ; Vasilevsky, Sergey F. ; Malysheva, Svetlana F. ; Kazheva, Olga N. ; Dyachenko, Oleg A. ; Kuimov, Vladimir A. / Tri(1-naphthyl)phosphine as a ligand in palladium-free Sonogashira cross-coupling of arylhalogenides with acetylenes. In: Heteroatom Chemistry. 2018 ; Vol. 29, No. 4.
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AU - Dyachenko, Oleg A.

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