N-Heterocyclic Carbene Catalyzed Photoenolization/Diels-Alder Reaction of Acid Fluorides.

Andreas Mavroskoufis Keerthana Rajes Paul GolzArush AgrawalVincent RußJan P Götze Matthew N Hopkinson

Published in: Angewandte Chemie (International ed. in English) (2020)

The combination of light activation and N-heterocyclic carbene (NHC) organocatalysis has enabled the use of acid fluorides as substrates in a UVA-light-mediated photochemical transformation previously observed only with aromatic aldehydes and ketones. Stoichiometric studies and TD-DFT calculations support a mechanism involving the photoactivation of an ortho-toluoyl azolium intermediate, which exhibits "ketone-like" photochemical reactivity under UVA irradiation. Using this photo-NHC catalysis approach, a novel photoenolization/Diels-Alder (PEDA) process was developed that leads to diverse isochroman-1-one derivatives.

Keyphrases

density functional theory
molecular dynamics
molecular dynamics simulations
room temperature
molecular docking
amino acid
radiation therapy
case control
structure activity relationship