91036-10-1Relevant articles and documents
One-Pot Electrochemical Nickel-Catalyzed Decarboxylative Sp2-Sp3 Cross-Coupling
Koyanagi, Takaoki,Herath, Ananda,Chong, Ashley,Ratnikov, Maxim,Valiere, Andrew,Chang, Jim,Molteni, Valentina,Loren, Jon
supporting information, p. 816 - 820 (2019/01/30)
A one-pot electrochemical nickel-catalyzed decarboxylative sp2-sp3 cross-coupling reaction has been developed using redox-active esters prepared in situ from alkyl carboxylates and N-hydroxyphthalimide tetramethyluronium hexafluorophosphate (PITU). This undivided cell one-pot method enables C-C bond formation using inexpensive, benchtop-stable reagents with isolated yields up to 95% with good functional group tolerance, which includes nitrile, ketone, ester, alkene and selectivity over other aromatic halogens.
Aryl Radicals from Electrochemical Reduction of Aryl Halides. Addition on Olefins
Chami, Zoubida,Gareil, Monique,Pinson, Jean,Saveant, Jean-Michel,Thiebault, Andre
, p. 586 - 595 (2007/10/02)
Aryl radicals generated by direct and indirect (by means of an aromatic anion radical mediator) electrochemistry are reacted with olefins in liquid ammonia and in organic solvents (Me2SO, MeCN, DMF).The arylated product is obtained in good yield in the latter case.In pure liquid NH3, the yields are extremely poor.They are improved upon addition of a proton donor such as urea or water; further increase of yields is obtained upon addition of 2-propanol.A reaction mechanism is proposed based on these observations and on the results of deuterium incorporation experiments.Cyclic voltammetry is used to determine the rate constant of the key step in the mechanism, viz, the addition of the aryl radical to the olefin, through its competition with its reaction with nucleophiles in the framework of an SRN1 substitution process.