1,2-Hydrogen atom transfer of aminyl radicals under photoredox catalysis for the synthesis of α-amino phosphine oxides
Year: 2025
Type: article
Abstract: deprotonation of N-centered radicals without the requirement of external strong bases, instead being facilitated by the benzoate anion generated during the reaction. This process enables the synthesis of α-amino phosphine oxides bearing various functional groups under mild conditions. The gram-scale synthesis demonstrates the scalability of the net 1,2-HAT rearrangement/radical-radical coupling reaction, which has been used in the preparation of an antitumor agent. Mechanistic investigations, including radical trapping experiments, Stern-Volmer fluorescence quenching experiments, cyclic voltammogram studies, cross-over experiments, KIE studies and DFT calculations support a net 1,2-HAT pathway.
Source: Chemical Science
DOI: 10.1039/d5sc00268k
Language: English
Subfield: Organic Chemistry
Field: Chemistry
Domain: Physical Sciences
Open Access status: diamond
Awards: Molecular Dynamics Investigation of the Reactivity of Alkyl Radicals in Transition Metal-Catalyzed Transformations, G2874908406, G3783944432, G3885390881, G3889766073, G4358336454, Applications of Chalcogen-based Oxidation State Alternating Organocatalysts, G6076405433, G739867569, Computation and Development of New, Enabling Synthetic Methods
OpenAlex ID: W4415928082