1188474-32-9Relevant academic research and scientific papers
Heterocyclization by catalytic carbonickelation of alkynes: A domino sequence involving vinylnickels
Durandetti, Muriel,Hardou, Lucie,Clement, Marie,Maddaluno, Jacques
, p. 4753 - 4755 (2009)
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
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.
