scholarly journals Electrochemically modified Corey–Fuchs reaction for the synthesis of arylalkynes. The case of 2-(2,2-dibromovinyl)naphthalene

2018 ◽  
Vol 14 ◽  
pp. 891-899 ◽  
Author(s):  
Fabiana Pandolfi ◽  
Isabella Chiarotto ◽  
Marta Feroci
Keyword(s):  
Electrochemical Reduction ◽  
Supporting Electrolyte ◽  
Cathodic Reduction ◽  
Terminal Alkyne ◽  
High Yields

The electrochemical reduction of 2-(2,2-dibromovinyl)naphthalene in a DMF solution (Pt cathode) yields selectively 2-ethynylnaphthalene or 2-(bromoethynyl)naphthalene in high yields, depending on the electrolysis conditions. In particular, by simply changing the working potential and the supporting electrolyte, the reaction can be directed towards the synthesis of the terminal alkyne (Et4NBF4) or the bromoalkyne (NaClO4). This study allowed to establish that 2-(bromoethynyl)naphthalene can be converted into 2-ethynylnaphthalene by cathodic reduction.

Regiospecific Palladium-Catalyzed Cross-Coupling Reactions Using the Operational Equivalent of 1,3-Dilithiopropyne

Synthesis ◽  
2020 ◽  
Vol 52 (16) ◽  
pp. 2387-2394 ◽  
Author(s):  
Jorge A. Cabezas ◽  
Natasha Ferllini
Keyword(s):  
Coupling Reaction ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Terminal Alkyne ◽  
Copper Iodide ◽  
Reaction Conditions ◽  
Cross Coupling Reactions ◽  
Cross Coupling Reaction ◽  
Palladium Catalyzed ◽  
High Yields

A regiospecific palladium-catalyzed cross-coupling reaction using the operational equivalent of the dianion 1,3-dilithiopropyne, with aromatic iodides is reported. This reaction gives high yields of 1-propyn-1-yl-benzenes and 2-(propyn-1-yl)thiophenes in the presence of catalytic amounts of palladium(0) or (II) and stoichiometric amounts of copper iodide. No terminal alkyne or allene isomers were detected. Reaction conditions were very mild and several functional groups were tolerated.

Voltammetry in the absence of excess supporting electrolyte – ECE-DISP1 reactions: The electrochemical reduction of 2-nitrobromobenzene in acetonitrile solvent

2011 ◽  
Vol 659 (1) ◽  
pp. 25-35 ◽  
Author(s):  
Edward O. Barnes ◽  
Yijun Wang ◽  
Juan G. Limon-Petersen ◽  
Stephen R. Belding ◽  
Richard G. Compton
Keyword(s):  
Electrochemical Reduction ◽  
Supporting Electrolyte

Inhibition Effects in the Electrochemical Reduction of Hydrogen Peroxide on Sodium Tungsten Bronzes

1974 ◽  
Vol 52 (14) ◽  
pp. 2542-2545 ◽  
Author(s):  
Jean-Paul Randin
Keyword(s):  
Hydrogen Peroxide ◽  
Electrochemical Reduction ◽  
Cathodic Reduction ◽  
Inhibition Effect ◽  
Surface Sites ◽  
Sodium Tungsten ◽  
Cathodic Side ◽  
Current Maximum ◽  
Current Potential

An inhibition effect has been observed during the cathodic reduction of hydrogen peroxide on sodium tungsten bronzes (NaxWO3). The effect is explained as competition for available surface sites between hydrogen peroxide and protons. The competing reaction is believed to be the formation of hydrogen bronze (NaxHzWO3). The experimental current–potential relationships fit with the theoretical curves calculated under Langmuirian conditions of adsorption to a point 30–40 mV on the cathodic side of the current maximum.

The Rise of Azide–Alkyne 1,3-Dipolar 'Click' Cycloaddition and its Application to Polymer Science and Surface Modification

2007 ◽  
Vol 60 (6) ◽  
pp. 384 ◽  
Author(s):  
Richard A. Evans
Keyword(s):  
Surface Modification ◽  
Atom Transfer Radical Polymerization ◽  
Historical Context ◽  
Dipolar Cycloaddition ◽  
Polymer Science ◽  
Surface Immobilization ◽  
Terminal Alkyne ◽  
New Methods ◽  
High Yields ◽  
Constant Interest

New methods to synthesize and functionalize polymers are of constant interest to the polymer scientist. The 1,3-dipolar cycloaddition between an azide and terminal alkyne has received much attention since the reports that copper(i) provides high yields and regioselective synthesis of 1,4-substituted 1,2,3-triazoles. This coupling chemistry has been rapidly adopted by polymer scientists in the synthesis and post-polymerization modification of polymers. This Review will provide the historical context of the recent development of the copper-mediated azide–alkyne cycloaddition and its use in polymer science, particularly in dendrimer synthesis/functionalization, surface immobilization/modification, orthogonally functionalizing polymers, and its integration with ATRP (atom transfer radical polymerization).

Metal-free chemoselective hydrogenation of unsaturated carbon–carbon bonds via cathodic reduction

2020 ◽  
Vol 7 (14) ◽  
pp. 1817-1822 ◽  
Author(s):  
Yongwei Qin ◽  
Jingjun Lu ◽  
Zirong Zou ◽  
Huanliang Hong ◽  
Yamei Li ◽  
...  
Keyword(s):  
Electrochemical Reduction ◽  
Selective Hydrogenation ◽  
Cathodic Reduction ◽  
Metal Free ◽  
Chemoselective Hydrogenation ◽  
Carbon Carbon Bonds ◽  
Carbon Bonds

A straightforward protocol for efficient and highly selective hydrogenation of unsaturated carbon–carbon bonds via electrochemical reduction has been reported.

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