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

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...

Environmentally Benign Microwave-Assisted Sonogashira Preparation of Aromatic Compounds

2011 ◽  
Vol 695 ◽  
pp. 113-116 ◽  
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.

Cu(II)-CMC: a mild, efficient and recyclable catalyst for the oxidative alkyne homocoupling reaction

2017 ◽  
Vol 72 (8) ◽  
pp. 549-554
Author(s):  
Yuqin Jiang ◽  
Niu Guo ◽  
Xiyong Li ◽  
Yamin Sun ◽  
Weiwei Zhang
Keyword(s):  
Catalytic Activity ◽  
Carboxymethyl Cellulose ◽  
Recyclable Catalyst ◽  
Sodium Carboxymethyl Cellulose ◽  
Terminal Alkynes ◽  
Mild Conditions ◽  
Efficient Route ◽  
Homocoupling Reaction ◽  
First Time

AbstractCu(II) heterogenized on sodium carboxymethyl cellulose (Na-CMC) has been thoroughly characterized by different techniques. Cu(II)-CMC has been applied for the first time in the homocoupling reaction of a variety of terminal alkynes. The catalyst furnished good to excellent yields of the desired products and could be reused six times without loss of catalytic activity. The Cu(II)-CMC catalysis protocol is a new efficient route to synthesize 1,3-diynes under mild conditions.

Cluster-based MOFs with accelerated chemical conversion of CO2 through C–C bond formation

2017 ◽  
Vol 53 (44) ◽  
pp. 6013-6016 ◽  
Author(s):  
Gang Xiong ◽  
Bing Yu ◽  
Jie Dong ◽  
Ying Shi ◽  
Bin Zhao ◽  
...  
Keyword(s):  
Heterogeneous Catalysts ◽  
Bond Formation ◽  
Chemical Conversion ◽  
Terminal Alkynes ◽  
Mild Conditions ◽  
First Time

We report here two cluster-based MOFs I and II as excellent heterogeneous catalysts in the carboxylation reactions of CO2 and terminal alkynes under 1 atm and mild conditions. This is the first time for MOFs materials to catalyze this type of reactions.

Mn(III)-Mediated Facile Access to Polysubstituted α-Naphthols from β-Keto Ester Derivatives and Terminal Alkynes

Synthesis ◽  
2020 ◽  
Vol 52 (13) ◽  
pp. 1959-1968
Author(s):  
Yuzhu Yang ◽  
Weidong Pan ◽  
Lisheng He ◽  
Fei Li ◽  
Xiaolan Liu
Keyword(s):  
Radical Cyclization ◽  
Terminal Alkynes ◽  
Keto Ester ◽  
Keto Esters ◽  
Mild Conditions ◽  
Cyclization Process ◽  
Reaction Proceeds ◽  
Mechanistic Investigations

A novel manganese-mediated reaction for the synthesis of polysubstituted α-naphthols has been developed from β-keto esters and terminal alkynes. This system holds the advantages of readily available starting materials and mild conditions. Mechanistic investigations revealed that this reaction proceeds via a tandem radical cyclization process.

scholarly journals Homocoupling of terminal alkynes catalyzed by CuCl under solvent-free conditions

2021 ◽  
pp. 174751982110325
Author(s):  
Yan Xiao ◽  
Jiyu Gao ◽  
Peng Chen ◽  
Guangliang Chen ◽  
Zicheng Li ◽  
...  
Keyword(s):  
Functional Group ◽  
Reaction Times ◽  
Environmentally Friendly ◽  
Solvent Free ◽  
Copper Salt ◽  
Terminal Alkynes ◽  
Mild Conditions ◽  
Solvent Free Conditions ◽  
Environmentally Friendly Process

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.

Copper and triphenylphosphine-promoted sulfenylation of quinones with arylsulfonyl chlorides

RSC Advances ◽  
2016 ◽  
Vol 6 (67) ◽  
pp. 62298-62301 ◽  
Author(s):  
Xiaoli Yu ◽  
Qiujin Wu ◽  
Huida Wan ◽  
Zhaojun Xu ◽  
Xingle Xu ◽  
...  
Keyword(s):  
Mild Conditions ◽  
First Time

The copper and triphenylphosphine-promoted sulfenylation of quinones with arylsulfonyl chlorides has been developed under mild conditions with moderate to good yields. This is the first time to prepare arylthioquinones with arylsulfonyl chlorides.

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

2013 ◽  
Vol 9 ◽  
pp. 1969-1976 ◽  
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.

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

ChemInform ◽  
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

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

Synthesis ◽  
2018 ◽  
Vol 50 (05) ◽  
pp. 1123-1132 ◽  
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.

Nitroacenaphthene as a New Photocatalyst for the Synthesis of Sulfonyl Amidines

Synthesis ◽  
2019 ◽  
Vol 51 (23) ◽  
pp. 4425-4433
Author(s):  
Yong Jian ◽  
Ming Chen ◽  
Chao Yang ◽  
Wujiong Xia
Keyword(s):  
Visible Light ◽  
Small Molecule ◽  
Reaction Pathways ◽  
Visible Light Photocatalyst ◽  
Mild Conditions ◽  
Sulfonyl Azides ◽  
Site Selective ◽  
First Time

A small molecule, namely nitroacenaphthene, is reported for the first time as a recyclable visible-light photocatalyst for the construction of the C=N bond from sulfonyl azides and amines. This scalable, site-selective protocol provides a convenient way to access various sulfonyl amidines under mild conditions. Two reaction pathways are proposed, according to different transformation patterns.

Sign in / Sign up

Export Citation Format

Share Document