Title:
N‐heterocyclic carbene catalyzed photoenolization/Diels–Alder reaction of acid fluorides
Author(s):
Mavroskoufis, Andreas; Rajes, Keerthana; Golz, Paul; Agrawal, Arush; Ruß, Vincent; Götze, Jan P.; Hopkinson, Matthew N.
Year of publication:
2019
Available Date:
2020-02-10T10:57:57Z
Abstract:
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.
Part of Identifier:
ISSN (print): 0044-8249
e-ISSN (online): 1521-3757
Keywords:
acid fluorides
N-heterocyclic carbenes
organocatalysis
photochemistry
photoenolization
DDC-Classification:
590 Tiere (Zoologie)
Publication Type:
Wissenschaftlicher Artikel
URL of the Original Publication:
DOI of the Original Publication:
Journaltitle:
Angewandte Chemie
Department/institution:
Biologie, Chemie, Pharmazie
Institut für Biologie / Arbeitsbereich Zoologie
