ChemInform Abstract: Efficient and Environmentally Friendly Glaser Coupling of Terminal Alkynes Catalyzed by Multinuclear Copper Complexes under Base-Free Conditions.

ChemInform ◽  
2016 ◽  
Vol 47 (31) ◽  
Author(s):  
Ling-Juan Zhang ◽  
Yan-Hong Wang ◽  
Jie Liu ◽  
Mei-Chen Xu ◽  
Xian-Ming Zhang
Keyword(s):  
Copper Complexes ◽  
Environmentally Friendly ◽  
Terminal Alkynes ◽  
Glaser Coupling

Efficient and environmentally friendly Glaser coupling of terminal alkynes catalyzed by multinuclear copper complexes under base-free conditions

RSC Advances ◽  
2016 ◽  
Vol 6 (34) ◽  
pp. 28653-28657 ◽  
Author(s):  
Ling-Juan Zhang ◽  
Yan-Hong Wang ◽  
Jie Liu ◽  
Mei-Chen Xu ◽  
Xian-Ming Zhang
Keyword(s):  
Catalytic System ◽  
Room Temperature ◽  
Copper Complexes ◽  
Coupling Reaction ◽  
Environmentally Friendly ◽  
Terminal Alkynes ◽  
Free Condition ◽  
Glaser Coupling

An efficient catalytic system with multinuclear copper complexes as catalysts has been developed for the aerobic Glaser coupling reaction, which adopts environmentally friendly water as the solvent at room temperature under base-free condition.

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.

scholarly journals Indol-2-Ylidene (IdY): A New Ambiphilic N-Heterocyclic Carbene Derived from Indole

2020 ◽  
Author(s):  
Hyunho Kim ◽  
Minseop Kim ◽  
Hayoung Song ◽  
Eunsung Lee
Keyword(s):  
Copper Complexes ◽  
Spectroscopic Studies ◽  
Elemental Selenium ◽  
Terminal Alkynes

The ambiphilic N-heterocyclic carbene ligand, indol-2-ylidene (IdY, <b>A</b>), is described. A series of indolenium precursors (<b>2a</b>-<b>f</b>) were prepared on a gram scale in good yields. Trapping experiments with elemental selenium, [RhCl(cod)]<sub>2</sub> and CuCl lead to IdY-supported materials, respectively. Computational and spectroscopic studies revealed the ambiphilicity of IdY. The copper complexes (<b>6</b>) show high percent buried volume (%V<sub>bur</sub> = 58.1) and allow for carboboration of terminal alkynes within 30 minutes as synthetically useful yields and high regioselectivity.

Metallomicelle catalyzed aerobic tandem desilylation/Glaser reaction in water

2019 ◽  
Vol 21 (11) ◽  
pp. 2899-2904 ◽  
Author(s):  
Shanyu Tang ◽  
Longjia Li ◽  
Xuanhe Ren ◽  
Jiao Li ◽  
Guanyu Yang ◽  
...  
Keyword(s):  
Copper Complexes ◽  
Nitrogen Ligands ◽  
Reaction In Water ◽  
Glaser Coupling

The copper complexes of PEG-grafted nitrogen ligands serve as metallomicellar nanoreactors for the aerobic tandem desilylation/Glaser coupling of TMS-protected alkynes in water.

Recent Advances in the Application of Nanometal Catalysts for Glaser Coupling

2020 ◽  
Vol 23 (22) ◽  
pp. 2489-2503 ◽  
Author(s):  
Saeideh Ebrahimiasl ◽  
Farnaz Behmagham ◽  
Shahrzad Abdolmohammadi ◽  
Rahman N. Kojabad ◽  
Esmail Vessally
Keyword(s):  
Transition Metal ◽  
Molecular Oxygen ◽  
Coupling Reaction ◽  
Terminal Alkynes ◽  
Oxidative Process ◽  
Copper Salts ◽  
Catalytic Systems ◽  
Transition Metal Nanoparticles ◽  
The Past ◽  
Glaser Coupling

: Synthesis of symmetrical 1,3-diynes from terminal alkynes through an oxidative process is generally called Glaser coupling. The classic Glaser coupling is catalyzed by copper salts under an atmosphere of molecular oxygen as an oxidant. Over the past years, different metal catalysts and oxidants were successfully used in this atom economical C-C coupling reaction. Moreover, several procedures for the preparation of unsymmetrical 1,3-diynes by coupling two different alkyne substrates have been developed. In this review, we will highlight the usefulness of transition metal nanoparticles as efficient catalysts in homo- and hetero-coupling of alkynes by hoping that it will be beneficial to the development of novel and extremely efficient catalytic systems for this fast-growing and important reaction.

Indium(III)-Catalyzed Transformations of Alkynes: Recent Advances in Carbo- and Heterocyclization Reactions

Synthesis ◽  
2017 ◽  
Vol 49 (22) ◽  
pp. 4931-4941 ◽  
Author(s):  
Nicklas Selander ◽  
Stalin Pathipati ◽  
Angela van der Werf
Keyword(s):  
Transition Metal ◽  
Environmentally Friendly ◽  
Short Review ◽  
Metal Catalysts ◽  
Transition Metal Catalysts ◽  
Nucleophilic Additions ◽  
Terminal Alkynes ◽  
Cyclization Reactions ◽  
Recent Advances

The use of a well-chosen catalyst is instrumental for the development of more efficient, economical and environmentally friendly reactions. In recent decades, indium-based catalysts have proven to be competitive and useful alternatives to transition-metal catalysts such as silver and gold. In this short review, we present some of the recent advances in indium(III)-catalyzed transformations of alkynes, with a focus on cyclization reactions.1 Introduction2 Terminal Alkynes as Nucleophiles3 Nucleophilic Additions to Alkynes4 Carbo- and Heterocyclization Reactions4.1 Carbocyclization4.2 Oxygen-Based Heterocycles4.3 Nitrogen-Based Heterocycles4.4 Sulfur-Based Heterocycles5 Conclusion

scholarly journals The effects of amines on oxidative homo-coupling of terminal alkynes promoted by copper salts

2005 ◽  
Vol 2005 (2) ◽  
pp. 112-115 ◽  
Author(s):  
Lei Wang ◽  
Jincan Yan ◽  
Pinhua Li ◽  
Min Wang ◽  
Caina Su
Keyword(s):  
Reaction Medium ◽  
Cross Coupling ◽  
Catalytic Amount ◽  
Sonogashira Reaction ◽  
Coupling Reactions ◽  
Sonogashira Coupling ◽  
Terminal Alkynes ◽  
Copper Salts ◽  
Terminal Acetylenes ◽  
Glaser Coupling

The effects of all kinds of amines on homo-couplings (Glaser reactions) of terminal alkynes promoted by copper salts and the Sonogashira coupling reactions were studied systematically. Diethylamine (2° amine) can serve as an excellent solvent, base and coordination ligand in the oxidative homo-coupling of terminal alkynes and several modified Glaser coupling procedures have been developed which are based on a catalytic amount of cuprous salts (CuI, CuBr or CuCl) with diethylamine systems. Homo-coupling of terminal acetylenes in the Sonogashira reaction could be inhibited by using triethylamine (3° amine) as reaction medium, and the cross-coupling products were formed as the exclusive products.

scholarly journals Environmentally Friendly Cp*Co(III)-catalyzed C-H Bond Hydroarylation of Alkynes

2021 ◽  
Vol 2076 (1) ◽  
pp. 012038
Author(s):  
JiaKai Zhao ◽  
Qi Mou ◽  
RuiHan Niu ◽  
RuYuan Zhao ◽  
Bo Sun
Keyword(s):  
Environmentally Friendly ◽  
High Yield ◽  
Synthetic Method ◽  
Terminal Alkynes

Abstract A facile synthetic method of Alkenylarene derivatives via cobalt(III)-catalyzed C-H hydroarylation with terminal alkynes has been presented. This helpful protocol provides a way to use terminal alkynes to couple with aryl groups through 1, 2-insertion, with high yield and good selectivity to obtain the corresponding hydroarylation products.

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