N‐Heterocyclic Carbene Catalyzed Photoenolization/Diels–Alder Reaction of Acid Fluorides | Zendy

Mavroskoufis Andreas | Zendy; Rajes Keerthana | Zendy; Golz Paul | Zendy; Agrawal Arush | Zendy; Ruß Vincent | Zendy; Götze Jan P. | Zendy; Hopkinson Matthew N. | Zendy

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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.

Publication year - 2020

Publication title -

angewandte chemie international edition

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 5.831

H-Index - 550

eISSN - 1521-3773

pISSN - 1433-7851

DOI - 10.1002/anie.201914456

Subject(s) - carbene , catalysis , diels–alder reaction , alder , chemistry , organic chemistry , botany , biology

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.

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