19017-03-9Relevant academic research and scientific papers
Selective N-Prop-2-ynylation of Heterocycles induced by Solid-Liquid Phase Transfer Catalysis without Solvent and Use of Solid Inorganic Supports
Galons, Herve,Bergerat, Isabelle,Combet-Farnoux, Claude,Miocque, Marcel,Decodts, Guy,Bram, Georges
, p. 1730 - 1731 (1985)
Complementary processes promote the N-prop-2-ynylation of heterocycles: solid-liquid phase transfer catalysis without added solvent in the presence or absence of alumina or titanium dioxide and alkylation on 'basic' alumina in 'dry media'.
Copper-Catalyzed Hydroamination of N-Allenylazoles: Access to Amino-Substituted N-Vinylazoles
Perego, Luca Alessandro,Blieck, Rémi,Michel, Julie,Ciofini, Ilaria,Grimaud, Laurence,Taillefer, Marc,Monnier, Florian
supporting information, p. 4388 - 4392 (2017/10/23)
Building on mechanistic studies, the innate capability of azoles to act as a directing group has been exploited to design an efficient and simple procedure for the hydroamination of N-allenylazoles with secondary amines. The reaction proceeds under mild conditions by copper(I) catalysis yielding the corresponding original linear E allylic amines with total regio- and stereoselectivity. Density Functional Theory (DFT) calculations offer a mechanistic explanation of the significantly higher reactivity of N-allenyl-(1,2)-azoles compared to their 1,3-analogues as a result of the reaction-enhancing coordination of the pyridine-like nitrogen to the copper center. (Figure presented.).
