1388044-76-5Relevant academic research and scientific papers
Convenient and practical alkynylation of heteronucleophiles with copper acetylides
Theunissen, Cedric,Lecomte, Morgan,Jouvin, Kevin,Laouiti, Anouar,Guissart, Celine,Heimburger, Jeremy,Loire, Estelle,Evano, Gwilherm
, p. 1157 - 1166 (2014/05/20)
Copper acetylides, readily available reagents which are characterized by their lack of reactivity, can be simply activated by oxidation with oxygen in the presence of simple nitrogen ligands such as TMEDA or imidazole derivatives. Upon activation, these nucleophilic species undergo a formal umpolung and can transfer their alkyne subunit to a wide range of heteronucleophiles, including amides, oxazolidinones, imines, and dialkyl phosphites. This alkynylation, which provides one of the most practical entry to useful building blocks such as ynamides, ynimines, and alkynylphosphonates, proceeds under especially mild conditions and can be easily performed on a multigram scale. Georg Thieme Verlag Stuttgart, New York.
Oxidative alkynylation of imines with alkynylcopper reagents: A straightforward and practical entry to ynimines
Laouiti, Anouar,Jouvin, Kvin,Bourdreux, Flavien,Rammah, Mohamedm.,Rammah, Mohamedb.,Evano, Gwilherm
experimental part, p. 1491 - 1500 (2012/06/16)
We have developed an efficient and general synthesis of ynimines based on an oxidative cross-coupling between imines and alkynylcopper reagents. Upon simple addition of 1,2-dimethylimidazole in the presence of oxygen, these bench-stable, crystalline, and readily available polymeric compounds were found to be especially suitable reagents for the introduction of an alkynyl group into a wide range of ketimines at room temperature and under especially mild conditions.
