Litcius/Paper detail

Transition metal-free photochemical C–F activation for the preparation of difluorinated-oxindole derivatives

Bianca T. Matsuo, Jadab Majhi, Albert Granados, Mohammed Sharique, Robert T. Martin, Osvaldo Gutiérrez, Gary A. Molander

2023Chemical Science47 citationsDOIOpen Access PDF

Abstract

-arylmethacrylamides for the preparation of valuable difluorinated oxindole derivatives. To achieve operational simplicity, the use of a readily available benzenethiol as a photocatalyst under open-to-air conditions was developed, demonstrating the facile multigram preparation of the targeted fluorinated molecules. Additionally, dispersion-corrected density functional theory (DFT) and empirical investigations provide a new basis to support the proposed reaction pathway, indicating that arene thiolate is an efficient organophotocatalyst for this transformation.

Topics & Concepts

OxindoleCombinatorial chemistryChemistryRadicalTransition metalDensity functional theoryMoleculeDispersion (optics)Computational chemistryCatalysisOrganic chemistryOpticsPhysicsFluorine in Organic ChemistryRadical Photochemical ReactionsSulfur-Based Synthesis Techniques