Light-driven, heterogeneous organocatalysts for C–C bond formation toward valuable perfluoroalkylated intermediates
Title
Light-driven, heterogeneous organocatalysts for C–C bond formation toward valuable perfluoroalkylated intermediatesAuthor(s)
Date
2020-11-11Citation
Citation: G. Filippini, F. Longobardo, L. Forster, A. Criado, G. Di Carmine, L. Nasi, C. D’Agostino, M. Melchionna, P. Fornasiero, M. Prato, Light-driven, heterogeneous orga-nocatalysts for novel C–C bond formation toward valuable perfluoroalkylated intermediates. Sci. Adv. 6, eabc9923 (2020).
Abstract
The favorable exploitation of carbon nitride (CN) materials in photocatalysis for organic synthesis requires the appropriate fine-tuning of the CN structure. Here, we present a deep investigation of the structure/activity relationship of CN in the photocatalytic perfluoroalkylation of organic compounds. Four types of CN bearing subtle structural differences were studied via conventional characterization techniques and innovative nuclear magnetic resonance (NMR) experiments, correlating the different structures with the fundamental mechanistic nexus and especially highlighting the importance of the halogen bond strength between the reagent and the catalyst surface. The optimum catalyst exhibited an excellent performance, with a very wide reaction scope, and could prominently trigger the model reaction using natural sunlight. The work lays a platform for establishing a new approach in the development of heterogeneous photocatalysts for organic synthesis related to medical, agricultural, and material chemistry.
Keywords
Graphitic carbon nitride
Hydrogen-peroxide
Oxygen reduction
Photocatalyst
Oxidation
Arenes
NMR
Iodoperfluoroalkylation
Pharmaceuticals
Heteroarenes
Characterization techniques
Structure/activity relationship
Hydrogen-peroxide
Oxygen reduction
Photocatalyst
Oxidation
Arenes
NMR
Iodoperfluoroalkylation
Pharmaceuticals
Heteroarenes
Characterization techniques
Structure/activity relationship
Editor version
Rights
Copyright © 2020 The Authors, some rights reserved; exclusive licensee American Association for the Advancement of Science. Distributed under a Creative Commons Attribution License 4.0 (CC BY).
ISSN
2375-2548 (eISSN)