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

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 language	English
Article number	e21443
Journal	Heteroatom Chemistry
Volume	29
Issue number	4
DOIs	https://doi.org/10.1002/hc.21443
Publication status	Published - 1 Jul 2018
Externally published	Yes

Keywords

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

ASJC Scopus subject areas

Chemistry(all)

Access to Document

10.1002/hc.21443

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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 journal › Article › peer-review

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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.",

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AU - Govdi, Anastasiya I.

AU - Vasilevsky, Sergey F.

AU - Malysheva, Svetlana F.

AU - Kazheva, Olga N.

AU - Dyachenko, Oleg A.

AU - Kuimov, Vladimir A.

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AB - 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.

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KW - tri(1-naphthyl)phosphine

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