Efficient hydroarylation of terminal alkynes with sodium tetraphenylborate performed in water under mild conditions

A series of symmetrical 1,4-disubstituted buta-1,3-diynes is prepared with excellent yields (up to 95%) through homocoupling of terminal alkynes catalyzed by a copper salt under solvent-free conditions. This method provides an environmentally friendly process to prepare 1,3-diynes in short reaction times under mild conditions. Furthermore, the method is suitable for a wide substrate scope and has excellent functional group compatibility. The reaction can also be scaled up to gram level.

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ChemInform Abstract: Palladium-Catalyzed Hydrophenylation of Alkynes with Sodium Tetraphenylborate under Mild Conditions.

ChemInform ◽

10.1002/chin.200820055 ◽

2008 ◽

Vol 39 (20) ◽

Author(s):

Hanxiang Zeng ◽

Ruimao Hua

Keyword(s):

Sodium Tetraphenylborate ◽

Mild Conditions ◽

Palladium Catalyzed

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Ni-catalyzed direct iminoalkynylation of unactivated olefins with terminal alkynes: facile access to alkyne-labelled pyrrolines

Organic Chemistry Frontiers ◽

10.1039/d1qo01217g ◽

2021 ◽

Author(s):

Xingjie Zhang ◽

Di Qi ◽

Chenchen Jiao ◽

Zhiguo Zhang ◽

Xiaopan Liu ◽

...

Keyword(s):

Radical Cyclization ◽

Terminal Alkynes ◽

Mild Conditions ◽

Type Coupling ◽

First Time

The direct iminoalkynylation of unactivated olefins with terminal alkynes is achieved for the first time by nickel-catalyzed cascade iminyl-radical cyclization/Sonogashira-type coupling of γ,δ-unsaturated oxime esters under mild conditions. This transformation...

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Gold-catalyzed reaction of oxabicyclic alkenes with electron-deficient terminal alkynes to produce acrylate derivatives

Beilstein Journal of Organic Chemistry ◽

10.3762/bjoc.9.233 ◽

2013 ◽

Vol 9 ◽

pp. 1969-1976 ◽

Cited By ~ 2

Author(s):

Yin-wei Sun ◽

Qin Xu ◽

Min Shi

Keyword(s):

Gold Catalyst ◽

Addition Product ◽

Terminal Alkynes ◽

Mild Conditions ◽

Ethynyl Ketone ◽

Oxabicyclic Alkenes

Oxabicyclic alkenes can react with electron-deficient terminal alkynes in the presence of a gold catalyst under mild conditions, affording the corresponding addition products in moderate yields. When using alkynyl esters as substrates, the (Z)-acrylate derivatives are obtained. Using but-3-yn-2-one (ethynyl ketone) as a substrate, the corresponding addition product is obtained with (E)-configuration. The proposed mechanism of these reactions is also discussed.

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ChemInform Abstract: Facile and Efficient Synthesis of 1-Haloalkynes via DBU-Mediated Reaction of Terminal Alkynes and N-Haloimides under Mild Conditions.

ChemInform ◽

10.1002/chin.201507081 ◽

2015 ◽

Vol 46 (7) ◽

pp. no-no

Author(s):

Mengru Li ◽

Yueju Li ◽

Baozhong Zhao ◽

Fushun Liang ◽

Long-Yi Jin

Keyword(s):

Terminal Alkynes ◽

Efficient Synthesis ◽

Mild Conditions

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Consecutive Multicomponent Reactions: Synthesis of 3-Acyl-4-alkynyl-Substituted 1,3-Thiazolidines

Synthesis ◽

10.1055/s-0036-1591873 ◽

2018 ◽

Vol 50 (05) ◽

pp. 1123-1132 ◽

Cited By ~ 2

Author(s):

Jürgen Martens ◽

Torben Schlüter ◽

Nils Frerichs ◽

Marc Schmidtmann

Keyword(s):

Functional Groups ◽

Multicomponent Reactions ◽

Terminal Alkynes ◽

Synthetic Route ◽

Acyl Chlorides ◽

Mild Conditions ◽

Three Component Reaction

This work describes the synthesis of compounds containing thiazolidine and propargylamidic motifs. Their preparation follows a synthetic route containing two multicomponent reactions. First, the Asinger four-component reaction is used to prepare 3-thiazolines and 3-oxazolines. Secondly, these heterocyclic imines are converted into propargylamides by a copper-catalyzed three-component reaction using acyl chlorides and terminal alkynes. The synthetic route is characterized by mild conditions and many functional groups are tolerated. The formation of an unexpected α-alkynoxyamide is also presented.

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Environmentally Benign Microwave-Assisted Sonogashira Preparation of Aromatic Compounds

Materials Science Forum ◽

10.4028/www.scientific.net/msf.695.113 ◽

2011 ◽

Vol 695 ◽

pp. 113-116 ◽

Cited By ~ 1

Author(s):

Suttikiat Puechmongkol ◽

Boonchoat Paosawatyanyong ◽

Worawan Bhanthumnavin

Keyword(s):

Coupling Reaction ◽

Environmentally Benign ◽

Conventional Heating ◽

Microwave Activation ◽

Sonogashira Coupling ◽

Terminal Alkynes ◽

Mild Conditions ◽

Aryl Bromides ◽

Sonogashira Coupling Reaction ◽

Type Coupling

An efficient Sonogashira-type coupling reaction of terminal alkynes and aryl bromides by microwave activation with short reaction time under mild conditions are presented. It is illustrated herein that the traditional Sonogashira coupling reaction can be achieved with a much more efficient yet environmentally friendly condition. In contrary to the usually required 10 mol% Pd loading and the use of conventional heating at 60 °C for 24 h in order for a reaction to proceed satisfactorily, with a 100 W microwave activation, the reaction of terminal alkynes with substituted aryl bromides can be achieved with only a 2.5 mol% Pd in 10 min. The yield was improved with microwave irradiation.

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