ChemInform Abstract: A Facile Copper(I)-Catalyzed Homocoupling of Terminal Alkynes to 1,3-Diynes with Diaziridinone under Mild Conditions

ChemInform ◽  
2014 ◽  
Vol 45 (10) ◽  
pp. no-no
Author(s):  
Yingguang Zhu ◽  
Yian Shi
Keyword(s):  
Terminal Alkynes ◽  
Mild Conditions

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.

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...

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.

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.

ChemInform Abstract: Enaminone Ligand-Assisted Homo- and Cross-Coupling of Terminal Alkynes under Mild Conditions.

ChemInform ◽  
2013 ◽  
Vol 44 (44) ◽  
pp. no-no
Author(s):  
Yunyun Liu ◽  
Chunping Wang ◽  
Xiaobo Wang ◽  
Jie-Ping Wan
Keyword(s):  
Cross Coupling ◽  
Terminal Alkynes ◽  
Mild Conditions

scholarly journals Synthesis of Stereodefined 1,1-Diborylalkenes via Copper-Catalyzed Diboration of Terminal Alkynes

2020 ◽  
Author(s):  
Yang Gao ◽  
Zhong-Qian Wu ◽  
Keary Engle
Keyword(s):  
Functional Group ◽  
Aryl Halides ◽  
Terminal Alkynes ◽  
Mild Conditions ◽  
Tandem Process ◽  
Trisubstituted Alkenes

A copper-catalyzed method for the <i>E</i>-selective 1,1-diboration of terminal alkynes is described. The tandem process involves sequential dehydrogenative borylation of the alkyne substrate with HBdan (HBdan = 1,8-diaminonaphthalatoborane), followed by hydroboration with HBpin (HBpin = pinacolborane). This method proceeds efficiently under mild conditions, furnishing 1,1-diborylalkenes with excellent stereoselectivity and broad functional-group tolerance. Taking advantage of the different reactivities of the two boryl moieties, the products can then be employed in stepwise cross-couplings with aryl halides for the stereocontrolled construction of trisubstituted alkenes.

Green Synthesis of Liquid Crystal Intermediates the Preparation of Phenylacetylenes in Ionic Liquids

2010 ◽  
Vol 428-429 ◽  
pp. 46-51
Author(s):  
Bao You Liu ◽  
Hui Long Yang ◽  
Yi Ping Wang ◽  
Yuan Yuan Wang ◽  
Zhi Jie Wu ◽  
...  
Keyword(s):  
Ionic Liquid ◽  
Ionic Liquids ◽  
Liquid Crystal ◽  
Green Synthesis ◽  
Sonogashira Coupling ◽  
Terminal Alkynes ◽  
Mild Conditions ◽  
Substituted Acetylenes

Sonogashira coupling of phenylacetylenes with phenyl iodides in 1-butyl-3-methyl- imidazolium bromide (BMImBr) was explored. Using CuI/Pd(PPh3)4 as a catalyst and Im as the base, the expected substituted acetylenes were obtained with good to excellent yields (61%-95%) under mild conditions (4h, 60oC). After the product was isolated, the left ionic liquid can been readily recovered and reused in the subsquent runs with almost the same efficiency. The reactivity of different iodoarenes with terminal alkynes was also discussed.

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