posted on 2021-11-11, 18:43authored byRolando Cannalire, Federica Santoro, Camilla Russo, Giulia Graziani, Gian Cesare Tron, Alfonso Carotenuto, Diego Brancaccio, Mariateresa Giustiniano
The merging of micellar
and photoredox catalysis represents a key
issue to promote “in water” photochemical transformations.
A photomicellar catalyzed synthesis of amides from N-methyl-N-alkyl aromatic amines and both aliphatic
and aromatic isocyanides is herein presented. The mild reaction conditions
enabled a wide substrate scope and a good functional groups tolerance,
as further shown in the late-stage functionalization of complex bioactive
scaffolds. Furthermore, solution 1D and 2D NMR experiments performed,
for the first time, in the presence of paramagnetic probes enabled
the study of the reaction environment at the atomic level along with
the localization of the photocatalyst with respect to the micelles,
thus providing experimental data to drive the identification of optimum
photocatalyst/surfactant pairing.