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

IF 1.1 4区化学 Q3 CHEMISTRY, MULTIDISCIPLINARY

Heteroatom Chemistry Pub Date : 2018-10-27 DOI:10.1002/hc.21443

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

引用次数: 5

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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三（1-萘基）膦作为配体参与芳基卤代物与乙炔的无钯Sonogashira交叉偶联

在超碱体系t-BuONa/DMSO中，以红磷和1-溴萘为原料，以34%的产率制备了三(1-萘基)膦(Np3P)。研究了以Np3P为配体，芳基碘化物与末端炔进行Sonogashira偶联合成芳基乙炔的简便方法。首次发现，与含供电子取代基的化合物反应时，较容易得到丁-1,3-二炔。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

Heteroatom Chemistry 化学-化学综合

CiteScore

1.20

自引率

0.00%

发文量

审稿时长

6 months

期刊介绍： Heteroatom Chemistry brings together a broad, interdisciplinary group of chemists who work with compounds containing main-group elements of groups 13 through 17 of the Periodic Table, and certain other related elements. The fundamental reactivity under investigation should, in all cases, be concentrated about the heteroatoms. It does not matter whether the compounds being studied are acyclic or cyclic; saturated or unsaturated; monomeric, polymeric or solid state in nature; inorganic, organic, or naturally occurring, so long as the heteroatom is playing an essential role. Computational, experimental, and combined studies are equally welcome. Subject areas include (but are by no means limited to): -Reactivity about heteroatoms for accessing new products or synthetic pathways -Unusual valency main-group element compounds and their properties -Highly strained (e.g. bridged) main-group element compounds and their properties -Photochemical or thermal cleavage of heteroatom bonds and the resulting reactivity -Uncommon and structurally interesting heteroatom-containing species (including those containing multiple bonds and catenation) -Stereochemistry of compounds due to the presence of heteroatoms -Neighboring group effects of heteroatoms on the properties of compounds -Main-group element compounds as analogues of transition metal compounds -Variations and new results from established and named reactions (including Wittig, Kabachnik–Fields, Pudovik, Arbuzov, Hirao, and Mitsunobu) -Catalysis and green syntheses enabled by heteroatoms and their chemistry -Applications of compounds where the heteroatom plays a critical role. In addition to original research articles on heteroatom chemistry, the journal welcomes focused review articles that examine the state of the art, identify emerging trends, and suggest future directions for developing fields.