TY - JOUR
T1 - Photomicellar Catalyzed Synthesis of Amides from Isocyanides: Optimization, Scope, and NMR Studies of Photocatalyst/Surfactant Interactions
AU - Cannalire, Rolando
AU - Santoro, Federica
AU - Russo, Camilla
AU - Graziani, Giulia
AU - TRON, Gian Cesare
AU - Carotenuto, Alfonso
AU - Brancaccio, Diego
AU - Giustiniano, Mariateresa
PY - 2022
Y1 - 2022
N2 - : 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.
AB - : 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.
UR - https://iris.uniupo.it/handle/11579/152722
U2 - 10.1021/acsorginorgau.1c00028
DO - 10.1021/acsorginorgau.1c00028
M3 - Article
SN - 2694-247X
VL - 2
SP - 66
EP - 74
JO - ACS ORGANIC & INORGANIC AU.
JF - ACS ORGANIC & INORGANIC AU.
IS - 1
ER -