Density Functional Theory Evaluation of a Photoinduced Intramolecular Aryl Ether Rearrangement.

ABSTRACT: Recently, a new approach of converting (hetero)aryl ethers to C-C coupled products via a photoinduced intramolecular rearrangement has been reported. Although this reaction is photocatalyst-free, it requires excitation in the ultraviolet (UV) range. To help refine this process, three different 2-(hetero)aryloxybenzaldehydes are selected from the available substrate scope in which the general mechanism based on experimental results is evaluated using density functional theory calculations. The reaction takes place in the triplet state after photoexcitation and includes three main steps: the addition of carbonyl carbon to the ipso carbon of the aryl ether followed by the C-O cleavage of the resulting spirocyclic intermediates and then the transfer of the formyl proton to afford 2-hydr

SUBMITTER: Feher PP 

PROVIDER: S-EPMC7880577 | biostudies-literature | 2021 Feb

REPOSITORIES: biostudies-literature