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A new synthetic pathway based on one-pot sequential aza-Michael addition and photoCuAAC click reactions

A solvent-free process is described for the synthesis of tailor-made molecules from a one-pot, two-step approach combining aza-Michael addition and photoinduced copper(i) catalysed azide–alkyne (photo-CuAAC) reactions. After the first reaction between an amine and an acrylate, cycloaddition between...

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Detalles Bibliográficos
Autores principales: Yin, Boyang, Croutxé-Barghorn, Céline, Delaite, Christelle, Allonas, Xavier
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2019
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9060615/
https://www.ncbi.nlm.nih.gov/pubmed/35514625
http://dx.doi.org/10.1039/c8ra10011j
Descripción
Sumario:A solvent-free process is described for the synthesis of tailor-made molecules from a one-pot, two-step approach combining aza-Michael addition and photoinduced copper(i) catalysed azide–alkyne (photo-CuAAC) reactions. After the first reaction between an amine and an acrylate, cycloaddition between an azide and an alkyne is activated by light irradiation in the presence of a copper complex. The kinetics of the aza-Michael addition and photo-CuAAC reaction were investigated by liquid state (1)H NMR spectroscopy and real-time Fourier transform infrared spectroscopy. This new process represents a well-defined spatio-temporal pathway to the synthesis of bespoke intermediate molecules for various applications.