1188474-27-2Relevant academic research and scientific papers
Nickel-Catalyzed Electrochemical Cyclization of Alkynyl Aryl Iodide and the Domino Reaction with Aldehydes
Déjardin, Claire,Renou, Amaury,Maddaluno, Jacques,Durandetti, Muriel
, p. 8882 - 8890 (2021/06/30)
An intramolecular carbometallation of a triple bond promoted by electrochemistry and mediated by nickel catalysis is described. This domino process transforms various aryl halides bearing a propargyl chain into substituted heterocycles in one single operation, with high stereoselectivities and in good to high yields. This reaction, characterized by a cyclic voltammetry set of experiments, proceeds following a syn-exo-dig cyclization process. When run at 80 °C, vinylbenzofuranes that are suitable substrates for cycloaddition reactions are obtained.
Synthetic applications of the nickel-catalyzed cyclization of alkynes combined with addition reactions in a domino process
Durandetti, Muriel,Hardou, Lucie,Lhermet, Rudy,Rouen, Mathieu,Maddaluno, Jacques
, p. 12773 - 12783 (2011/12/04)
Carbonickelations of alkynes and functionalization of the resulting vinylnickel moiety have been performed efficiently in a nickel-catalyzed domino cyclization-condensation process. This reaction, which does not require the preparation of any other organometallic reagent, proceeds only by exo-dig cyclization. This convenient and mild method constitutes a one-pot synthesis of substituted dihydrobenzofurans, chromans, isochromans, indoles, or indanes. Theses valuable products are generally obtained in good yields and high stereoselectivity. They are shown to be useful synthons for rapid access to functionalized polycyclic skeletons. Yes nickel can! Carbonickelation of alkynes and functionalization of the resulting vinylnickel moiety occurs efficiently. Overall, a domino cyclization-condensation process propagated by substoichiometric nickel catalysis takes place (see scheme). This one-pot synthesis provides substituted polyheterocyclic compounds in good yields and high stereoselectivity.
Heterocyclization by catalytic carbonickelation of alkynes: A domino sequence involving vinylnickels
Durandetti, Muriel,Hardou, Lucie,Clement, Marie,Maddaluno, Jacques
supporting information; experimental part, p. 4753 - 4755 (2010/01/15)
Reaction of Ni(0) in the presence of iodoarylethers 1 leads, after syn intramolecular carbonickelation of the triple bond, to nucleophilic vinylnickels which can be trapped, in a tandem process, by various electrophiles introduced at the onset of the reac
