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

Boyang YinCéline Croutxé-BarghornChristelle DelaiteXavier Allonas
Published in: RSC advances (2019)
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.
Keyphrases
  • electron transfer
  • ionic liquid
  • atomic force microscopy