1190789-03-7Relevant academic research and scientific papers
Versatile Access to Tetrasubstituted 2-Amidoacroleins through Formal Silylformylation of Ynamides
Donnard, Morgan,Golling, Stéphane,Leroux, Frédéric R.
supporting information, p. 8093 - 8097 (2021/10/25)
In this paper we are reporting the first regio- and stereoselective silylformylation of ynamides. This reaction is tolerant to a wide range of functional groups around the ynamides. The substitution of CO by an isocyanide makes this reaction safer and mor
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.
Preparation of multisubstituted enamides via rhodium-catalyzed carbozincation and hydrozincation of ynamides
Gourdet, Benoit,Rudkin, Mairi E.,Watts, Ciorsdaidh A.,Hon, Wai Lam
supporting information; experimental part, p. 7849 - 7858 (2010/01/16)
(Chemical Equation Presented) Rhodium-catalyzed carbozincation of ynamides using diorganozinc reagents or functionalized organozinc halides is described.Using a tri(2-furyl)phosphine-modified rhodium catalyst, the reaction course is altered to hydrozincation when diethylzinc is employed as the organozinc reagent. Trapping of the alkenylzinc intermediates produced in these reactions in further functionalization reactions is possible. Collectively, these processes enable access to a range of multisubstituted enamides in stereo- and regiocontrolled fashion.
