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Difluoroalkylation of Anilines via Photoinduced Methods

Albert Gallego‐Gamo, Albert Granados, Roser Pleixats, Carolina Gimbert‐Suriñach, Adelina Vallribera

2023The Journal of Organic Chemistry15 citationsDOIOpen Access PDF

Abstract

The development of sustainable and mild protocols for the fluoroalkylation of organic backbones is of current interest in chemical organic synthesis. Herein, we present operationally simple and practical transition-metal-free methods for the preparation of difluoroalkyl anilines. First, a visible-light organophotocatalytic system working via oxidative quenching is described, providing access to a wide range of difluoroalkyl anilines under mild conditions. In addition, the formation of an unprecedented electron donor-acceptor (EDA) complex between anilines and ethyl difluoroiodoacetate is reported and exploited as an alternative, efficient, and straightforward strategy to prepare difluoroalkyl derivatives.

Topics & Concepts

Combinatorial chemistryOrganic synthesisQuenching (fluorescence)ChemistryAcceptorRadicalPhotochemistryOrganic chemistryCatalysisFluorescencePhysicsCondensed matter physicsQuantum mechanicsFluorine in Organic ChemistryRadical Photochemical ReactionsInorganic Fluorides and Related Compounds
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